Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Six-membered Hetero Ring (e.g., Lysergic Acid, Etc.) Patents (Class 546/69)
  • Patent number: 4547500
    Abstract: A 2-methyl-8 (R) or (S) ergot peptide alkaloid in free base form or in pharmaceutically acceptable acid addition salt form is a useful anti-Parkinson agent, prolactin secretion inhibitor, anti-depressant, vigilance-increasing agent, and anti-migraine agent.
    Type: Grant
    Filed: May 10, 1983
    Date of Patent: October 15, 1985
    Assignee: Sandoz Ltd.
    Inventors: Georg Bolliger, Peter Stutz
  • Patent number: 4542135
    Abstract: 9-Thia ergot cyclic peptide alkaloids produced by fermentation or synthetic methods have interesting anti-parkinson and other pharmacological activities.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: September 17, 1985
    Assignee: Sandoz Ltd.
    Inventors: Hans Kobel, Jean-Jacques Sanglier, Hans Tscherter, Georg Bolliger
  • Patent number: 4526892
    Abstract: Novel ergoline derivatives formed by reaction of an 8-carboxy ergoline with a carbodiimide and having hypotensive and antiprolatinic activity.
    Type: Grant
    Filed: December 9, 1982
    Date of Patent: July 2, 1985
    Assignee: Farmitalia Carlo Erba, S.p.A.
    Inventors: Patricia Salvati, Anna M. Caravaggi, Aldemio Temperilli, Germano Bosisio, Osvaldo Sapini, Enrico di Salle
  • Patent number: 4524208
    Abstract: A process for preparing lysergic acid esters of the formula ##STR1## wherein R is alkyl of up to 3 carbon atoms, comprises reacting corresponding lysergic acid or isolysergic acid amides with corresponding alcohols at temperatures of 0.degree. to 65.degree. C. for 2 to 30 hours in the presence of an acid at a pH value of 0-1.
    Type: Grant
    Filed: May 26, 1983
    Date of Patent: June 18, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Gerhard Sauer, Gregor Haffer
  • Patent number: 4515950
    Abstract: The invention concerns a process for the isomerization of ergoline derivatives substituted in the 8.beta. position by an electron withdrawing radical to the corresponding 8.alpha. compounds by removal of the proton in the 8.alpha. position and by a following, separately effected, protonation.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: May 7, 1985
    Assignee: Sandoz Ltd.
    Inventors: Zdenek Brich, Herbert Muhle
  • Patent number: 4491664
    Abstract: A process for the production of an ergot alkaloid comprising intramolecularly cyclizing a 3-iminoethyl-4-trans-buta-1',3'-dienylindole to produce an 8-ergolene and as necessary converting the resultant ergolene into the desired ergot alkaloid.
    Type: Grant
    Filed: March 12, 1982
    Date of Patent: January 1, 1985
    Assignee: Sandoz Ltd.
    Inventor: Wolfgang Oppolzer
  • Patent number: 4417051
    Abstract: A process for preparing an 8.alpha.-substituted 6-methyl-10.alpha.-H-ergoline of the formula ##STR1## wherein R.sub.1 is HN--CO--NX.sub.2 (wherein X is hydrogen, methyl or ethyl), CO--NH--NX.sub.2, CO--NX.sub.2, or CH.sub.2 OX, comprises reducing the corresponding 8.alpha.-substituted-9,10-didehydro-6-methylergoline, with an alkali metal or alkaline earth metal dissolved in a nitrogen compound which is a primary or secondary C.sub.1-3 -alkylamine, a hexa-C.sub.1-2 -alkyl-phosphoric triamide or ammonia at a temperature of -70.degree. to -30.degree. C.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: November 22, 1983
    Assignee: Schering, Aktiengesellschaft
    Inventor: Gerhard Sauer
  • Patent number: 4249001
    Abstract: Prostanoic acid ergolinylalkyl-esters, -thioesters and -amides have interesting prostaglandin-like activity, especially blood pressure lowering activity.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: February 3, 1981
    Assignee: Sandoz Ltd.
    Inventor: Roland Wenger
  • Patent number: 4248871
    Abstract: The present invention provides compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine andY is hydrogen or bromine, with the proviso that when X is chlorine Y is hydrogen,Z is carbonyl or sulphonyl,R.sub.1 is alkyl of 1 to 4 carbon atoms, andeither (i)R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, andR.sub.3 is hydrogen, alkyl of 1 to 5 carbon atoms, or phenyl,or (ii)R.sub.2 together with R.sub.3 is a radical of formula ##STR2## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are, independently, hydrogen or alkyl of 1 to 4 carbon atoms,or (iii)R.sub.2 together with R.sub.4 is a radical of formula--(CH.sub.2).sub.2 --A--(CH.sub.2).sub.2 --wherein A is a bond, oxygen, sulphur or NR.sub.8 wherein R.sub.8 is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or alkoxyphenyl,useful as venotonising agents.
    Type: Grant
    Filed: June 4, 1979
    Date of Patent: February 3, 1981
    Assignee: Sandoz Ltd.
    Inventor: Paul Stadler
  • Patent number: 4237291
    Abstract: A process for isolating ergot alkaloids from culture suspensions, in which after mechanical filtration, the residue is dried in a fluidized drying bed and the alkaloids are extracted with an aprotic organic solvent, reextracted with a weakly acidic aqueous solution which is subsequently made basic, and finally extracted with a water-immiscible organic solvent, from which the alkaloids are isolated in a conventional manner. In certain instances, the culture suspension is stirred with an adsorbent clay to entrain the water-soluble alkaloids.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: December 2, 1980
    Assignee: VEB Arzneimittelwerk Dresden
    Inventors: Werner Grawert, Ludwig Schiedt, Brigitte Neumann, Karlheinz Heidenbluth, Christoph Dauth, Rudolf Schirutschke, Monika Muller
  • Patent number: 4230859
    Abstract: A process for the preparation of N-substituted esters of 9,10-dihydrolysergic acids of the formula: ##STR1## wherein R.sub.1 is an alkyl group of 1-5 carbon atoms, an alkenyl group of 2-5 carbon atoms or a cycloalkyl group of 3-5 carbon atoms,R.sub.2 is hydrogen or an alkoxy group of 1-3 carbon atoms andX' is hydrogen or halogen,characterized in that esterified 9,10-dihydrolysergic acids of the formula: ##STR2## wherein R is hydrogen or a hydrolyzable organic group,X' is hydrogen or halogen, andR.sub.2 has the meaning as stated above,are reacted with a compound of the formula:R.sub.1 Y (III)whereinR.sub.1 has the meaning as stated above,Y is halogen or sulphate,in the presence of a catalyst for phase transition in the presence of aqueous alkali medium in an inert organic solvent immiscible with water, and certain novel esters obtained thereby.
    Type: Grant
    Filed: July 7, 1978
    Date of Patent: October 28, 1980
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventor: Rudolf Rucman
  • Patent number: 4229451
    Abstract: This invention provides new compounds of formula I, ##STR1## wherein R is branched chain alkyl of 3 to 6 carbon atoms, useful as venoconstrictors and venotonics.
    Type: Grant
    Filed: June 29, 1978
    Date of Patent: October 21, 1980
    Assignee: Sandoz Ltd.
    Inventors: Theodor Fehr, Paul Stadler
  • Patent number: 4201862
    Abstract: 2-Azaergolines, 2-aza-8(or 9)-ergolenes, neuroleptic agents.
    Type: Grant
    Filed: March 16, 1979
    Date of Patent: May 6, 1980
    Assignee: Eli Lilly and Company
    Inventors: Edmund C. Kornfeld, Nicholas J. Bach
  • Patent number: 4197299
    Abstract: A method for preparing ergoline derivatives in which the ergoline structure is variously substituted by morpholino-piperazino- and other active radicals to obtain novel compounds useful in cardiology as alpha-blocking, vasodilating, antihypertensive active ingredients of pharmaceutical preparations.
    Type: Grant
    Filed: June 20, 1978
    Date of Patent: April 8, 1980
    Assignee: Simes Societa Italiana Medicinali e Sintetici
    Inventors: Giorgio Ferrari, Vittorio Vecchietti
  • Patent number: 4196288
    Abstract: New ergoline derivatives are disclosed which are compounds of formula (I) having the structure: ##STR1## wherein R.sub.1 is hydrogen or methoxy; R.sub.2 is hydrogen or methyl; andX is hydroxy, R.sub.3 COO, S--R.sub.4 or NR.sub.5 R.sub.6 in which R.sub.3 is a straight or branched alkyl having from 1 to 6 carbon atoms, unsubstituted- or substituted-phenyl, the substituents being selected from the class consisting of chlorine, bromine, alkyl or alkoxy having from 1 to 4 carbon atoms, cycloalkyl containing from 3 to 6 carbon atoms, or a heterocycle;R.sub.4 is phenyl or a heterocycle, andR.sub.5 and R.sub.6 are alkyl having from 1 to 4 carbon atoms, or together with the N atom to which they are attached, forming a heterocycle.
    Type: Grant
    Filed: December 1, 1977
    Date of Patent: April 1, 1980
    Assignee: Societa Farmaceutici Italia S.p.A.
    Inventors: Enzo Beacco, Luigi Bernardi, Enrico Di Salle, Giovanni Falconi, Bianca Patelli
  • Patent number: 4195086
    Abstract: This invention provides new compounds of formula I, ##STR1## wherein R.sub.1 is alkyl or 2 to 5 carbon atoms, andR.sub.2 is methyl or ethyl,useful as anti-migraine agents and for the treatment of orthostatic disorders.
    Type: Grant
    Filed: July 26, 1978
    Date of Patent: March 25, 1980
    Assignee: Sandoz Ltd.
    Inventors: Theodor Fehr, Paul Stadler
  • Patent number: 4180581
    Abstract: The present invention provides compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine andY is hydrogen or bromine, with the proviso that when X is chlorine Y is hydrogen,Z is carbonyl or sulphonyl,R.sub.1 is alkyl of 1 to 4 carbon atoms, andeither (i)R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, andR.sub.3 is hydrogen, alkyl of 1 to 5 carbon atoms, or phenyl,or (ii)R.sub.2 together with R.sub.3 is a radical of formula ##STR2## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are, independently, hydrogen or alkyl of 1 to 4 carbon atoms,or (iii)R.sub.2 together with R.sub.4 is a radical of formula--(CH.sub.2).sub.2 --A--(CH.sub.2).sub.2 --wherein A is a bond, oxygen, sulphur or NR.sub.8 wherein R.sub.8 is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or alkoxyphenyl,useful as venotonising agents.
    Type: Grant
    Filed: January 26, 1978
    Date of Patent: December 25, 1979
    Assignee: Sandoz Ltd.
    Inventor: Paul Stadler
  • Patent number: 4145549
    Abstract: The present invention provides a novel cyclization process useful for the production of the peptide moiety of an ergotalkaloid.
    Type: Grant
    Filed: January 7, 1977
    Date of Patent: March 20, 1979
    Assignee: Sandoz Ltd.
    Inventor: Paul Stadler
  • Patent number: RE30218
    Abstract: 8,8-Disubstituted-6-methylergolines and 9-ergolenes, prepared by alkylation of lysergic, isolysergic or their 9,10-dihydro analogues, optionally followed by chemical modification of an 8-substituent.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: February 19, 1980
    Assignee: Eli Lilly and Company
    Inventors: Nicholas J. Bach, Edmund C. Kornfeld
  • Patent number: RE30219
    Abstract: 8,8-Disubstituted-6-methylergolines and 9-ergolenes, are prepared by alkylation of lysergic, or isolysergic acid or their 9,10-dihydro analogues.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: February 19, 1980
    Assignee: Eli Lilly and Company
    Inventors: Nicholas J. Bach, Edmund C. Kornfeld