Chalcogen Or Nitrogen Bonded Directly To Ring Carbon Of The Six-membered Hetero Ring Patents (Class 546/68)
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Patent number: 4874768Abstract: The disclosure relates to 1,2-substituted ergoline derivatives of general Formula I ##STR1## wherein X is an oxygen or sulfur atom,R.sup.1 is a lower alkyl group,R.sup.2 is halogen, acyl, a saturated or unsaturated lower alkyl group which can optionally be substituted by OR.sup.4 wherein R.sup.4 is hydrogen, lower alkyl, tetrahydropyranyl or cycloalkyl, or by an optionally substituted aryl residue, an S-R.sup.5 -group wherein R.sup.5 means a lower alkyl group which can optionally be substituted by aryl or an optionally substituted aryl residue, a ##STR2## wherein n=2 o4 3, or a --CHO-group, R.sup.3 is lower alkyl or acyl, andC.sub.9 -C.sub.10 is a CC-single or a CC-double bond, and the hydrogen atom in the 10-position is in the .alpha.-location if C.sub.9 -C.sub.10 is a CC-single bond, as well as the acid addition salts thereof. The compounds exhibit valuable pharmacological properties.Type: GrantFiled: October 6, 1986Date of Patent: October 17, 1989Assignee: Schering AktiengesellschaftInventors: Andreas Huth, Gerhard Sauer, Helmut Wachtel
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Patent number: 4863929Abstract: Novel 12- and 13-substituted ergoline derivatives are suitable, e.g., as psychopharmaceuticals and for hypertension therapy.Type: GrantFiled: September 19, 1986Date of Patent: September 5, 1989Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Josef Heindl, Gertrud Schroeder, Helmut Wachtel
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Patent number: 4859678Abstract: An ergoline derivative of the formula I: ##STR1## wherein R.sub.1 represents hydrogen or a methyl group; R.sub.2 represents hydrogen or a halogen atom, a methyl, cyano or phenyl group or an alkylthio group having from 1 to about 4 carbon atoms; R.sub.3 represents a hydrocarbon group having from 1 to about 4 carbon atoms; R.sub.4 represents hydrogen, a phenyl group or a hydrocarbon group having from 1 to about 4 carbon atoms; wherein either (a) R.sub.6 and R.sub.7 represent a valence bond or hydrogen atoms and R.sub.8 represents a hydrogen atom or a methoxy group, or (b) R.sub.6 represents a hydrogen atom and R.sub.7 and R.sub.8 taken together represent a valence bond; W represents an oxygen atom or an imino group; A represents a group of the formula CHR.sub.5, CH.dbd.CR.sub.5 or CH.sub.2 CHR.sub.5 wherein R.sub.Type: GrantFiled: June 21, 1988Date of Patent: August 22, 1989Assignee: Farmitalia Carlo ErbaInventors: Sergio Mantegani, Enzo Brambilla, Aldemio Temperilli, Daniela Ruggieri, Patricia Salvati
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Patent number: 4857298Abstract: Compounds of general Formula I labeled with .sup.121 I, .sup.122 I, .sup.123 I, .sup.124 I, .sup.125 I, .sup.131 I and .sup.132 I isotopes ##STR1## wherein R.sup.6 is a C.sub.1-6 aliphatic hydrocarbon residue andC.sub.2 -C.sub.3 C.sub.9 -C.sub.10 is a single or a double bond, as well as their acid addition salts,are useful as diagnostic media, e.g., in imaging dopamine and other receptors.Type: GrantFiled: July 10, 1987Date of Patent: August 15, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Wachtel, Herbert H. Schneider, Peter-Andreas Loschmann, Rainer Dorow, Reinhard Horowski, Bernard Acksteiner, Paul-Eberhard Schulze, Gerhard Sauer
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Patent number: 4853390Abstract: (2-Haloergolinyl)-N',N'-diethylurea derivatives of Formula I ##STR1## and the salts thereof, wherein R is hydrogen, alkyl of up to 6 carbon atoms, or alkenyl of up to 3 carbon atoms,X is halogen, ##STR2## is a CC single or CC double bond, and the urea residue in the 8-position can be in the .alpha.- or .beta.-configuration, have neuropsychotropic properties.As a result, they are excellently suitable for treatment of psychotic disturbances and emesis.Type: GrantFiled: March 2, 1987Date of Patent: August 1, 1989Assignee: Schering AktiengesellschaftInventors: Jean-Claude Hilscher, Wolfgang Kehr, Gerhard Sauer, Herbert Schneider, Helmut Wachtel
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Patent number: 4847262Abstract: Novel ergoline derivatives, substituted in the 2-position, of the formula ##STR1## wherein C.sub.8 ---C.sub.9 and C.sub.9 ---C.sub.10 each independently is a CC-single or a C.dbd.C-double bond, but not together a cumulated double bond, and the substituent in the 8-position is in the .alpha.- or .beta.-configuration where C.sub.8 ---C.sub.9 is a CC-single bond,R.sup.2 is a CN, SR, SOR, ##STR2## wherein n is 2 or 3, ##STR3## and --CH(OR)R whereinR has the meaning of H or C.sub.1-4 -alkyl,the grouping COR' and CSR'wherein R'=OH, OC.sub.1-4 -alkyl, benzyl, NH.sub.2 or NHR",the grouping CH.dbd.CH--CO.sub.2 R" and CH.sub.2 --CH.sub.2 --CO.sub.2 R'wherein R"=C.sub.1-4 -alkyl,the grouping C.tbd.C--R'" and HC.dbd.CH--R'"wherein R'"=hydrogen, C.sub.1-4 -alkyl, phenyl, CH.sub.2 OH, CR".sub.2 OH, ##STR4## CO.sub.2 R", CH.sub.2 NR".sub.2 or SiMe.sub.2 R"; C.sub.1-3 -alkyl, or C.sub.1-3 -alkyl substituted by OH or phenyl; or ##STR5## wherein R" is C.sub.1-4 alkyl, R.sup.6 is C.sub.1-4 -alkyl andR.sup.Type: GrantFiled: December 22, 1987Date of Patent: July 11, 1989Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Andreas Huth, Helmut Wachtel, Herbert H. Schneider
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Patent number: 4841056Abstract: There are disclosed intermediates to pharmaceutical compounds of the formula ##STR1## in which R.sup.1 is an aliphatic or aromatic function, and R.sup.2 and R.sup.3 are each hydrogen, C.sub.1-4 alkyl or a protecting group; and salts thereof.Type: GrantFiled: January 27, 1988Date of Patent: June 20, 1989Assignee: Lilly Industries LimitedInventor: William H. Hunter
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Patent number: 4826851Abstract: Novel 2-substituted ergolinyl urea and thioruea derivatives are disclosed, as well as their use as pharmaceuticals, specifically as neuroleptics. The compounds, which possess central dopaminergic activity, have the formula ##STR1## wherein X is an oxygen or sulfur atom,R.sup.1 is a lower alkyl group,Y is a sulfur atom, S--CH.sub.2 --, C.sub.2 H.sub.4 --, --CH.dbd.CH--, or --C.tbd.C--,R.sup.2 is an aromatic ring of 5-6 atoms, 0-3 of which are O, S or N; or an aromatic ring of 5-6 atoms, 0-3 of which are O, S or N, and which is substituted by C.sub.1-2 -alkyl, C.sub.1-2 -alkoxy, nitrile, nitro, amino, C.sub.1-2 -alkylamino, carbonylamino or halo group, andC.sub.9 C.sub.10 is a CC-single or a CC-double bond and, if C.sub.9 C.sub.10 means a CC-single bond, the hydrogen atom in the 10-position is in the .alpha.-location,or a pharmaceutically acceptable acid addition salt thereof, wherein, if X is an oxygen atom, R.sup.1 is methyl and C.sub.9 C.sub.10 is a single bond, Y--R.sup.2 does not mean --C.sub.2 H.sub.Type: GrantFiled: October 6, 1986Date of Patent: May 2, 1989Assignee: Schering AktiengesellschaftInventors: Andreas Huth, Gerhard Sauer, Helmut Wachtel
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Patent number: 4826852Abstract: Ergolinyl compounds which are nitrogen-substituted in the 8-position and have Formula (I) ##STR1## and physiologically compatible salts thereof, wherein (a) R.sup.1 is hydrogen, the 8-substituent can be in the .alpha.- or .beta.-position and ##STR2## represents a single or a double bond, R.sup.2 is hydrogen, C.sub.1-4 -alkyl or C.sub.1-7 -acyl,R.sup.3 is hydrogen, chlorine or bromine, andR.sup.4 is C.sub.1-6 -alkyl, C.sub.3-6 -cycloalkyl-C.sub.1-3 -alkyl, C.sub.3-6 -alkenyl, or C.sub.3-6 -alkynyl; or(b) R.sup.1 is ##STR3## and the 8-substituent can be in the .alpha.- or .beta.-position, ##STR4## represents a single or double bond, R.sup.2, R.sup.3 are as defined above,R.sup.4, is C.sub.1.varies.6 -alkyl, C.sub.3-6 -cycloalkyl-C.sub.1-3 -alkyl, C.sub.3-6 -alkenyl, or C.sub.3-6 -alkynyl; andR.sup.5 is hydrogen, C.sub.-10 -alkyl, C.sub.3-10 -alkenyl, or C.sub.3-10 -alkynyl, andR.sup.6 is C.sub.1-10 -alkyl, C.sub.3-10 -alkenyl, C.sub.3-10 -alkynyl, or aryl, orR.sup.5 and R.sup.Type: GrantFiled: June 26, 1986Date of Patent: May 2, 1989Assignee: Schering AktiengesellschaftInventors: Gregor Haffer, Gerhard Sauer, Helmut Wachtel, Herbert Schneider, Ulrich Eder
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Patent number: 4816587Abstract: The invention relates to a novel process for the halogenation in 2-position of ergot alkaloids. The process is characterized by that as a halogenating agent a system consisting of dimethylsulfoxide, a trialkylhalosilane or triarylhalosilane and optionally a hydrogen halide is used.Type: GrantFiled: June 5, 1987Date of Patent: March 28, 1989Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Gabor Megyeri, Tibor Keve, Lajos Kovacs, Jr., Bela Stefko, Erik Bogsch, Anna Kassia nee Zieger, Ferenc Trischler, Gabor Szepesi, Maria Gazdag
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Patent number: 4801714Abstract: Ergolinylthioureas derivatives of the general Formula I ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or acyl,R.sup.2 is hydrogen, halogen or a lower alkylthio groupR.sup.3 is lower alkyl,R.sup.4, R.sup.5 and R.sup.6, is hydrogen or lower alkyl, and each is identical or different,n=0, 1 or 2 and C.sub.9 --C.sub.10 is a single or a double bond; are produced by reacting in an ergolin-8-ylurea compound otherwise corresponding to Formula I with a --CO--NR.sup.5 R.sup.6 group in place of the --CS--Nr.sup.5 R.sup.6 group is reacted with a chlorinating agent and a thiolating agent.Type: GrantFiled: August 6, 1986Date of Patent: January 31, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Gregor Haffer
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Patent number: 4791116Abstract: The present invention provides N,N-Diethyl-N'-[(8.alpha.)-1-ethyl-6-methyl-ergolin-8-yl]-sulfamide, and N,N-Diethyl-N'-[(8.alpha.)-1-isopropyl-6-methyl-ergolin-8-yl)-sulfamide useful as prolactin secretion inhibiton, anti-parkinson agents and anti-depressant agents.Type: GrantFiled: December 1, 1986Date of Patent: December 13, 1988Assignee: Sandoz Ltd.Inventor: Paul Pfaffli
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Patent number: 4791115Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl, R.sub.2 is hydrogen, chlorine, bromine or methyl, R.sub.3 is C.sub.1-5 alkyl or C.sub.3-5 alkenyl and R.sub.4 is C.sub.1-7 alkyl; C.sub.3-7 cycloalkyl; adamantyl; or optionally substituted phenyl, are useful as neuroleptic agents and PRL secretion inhibitors.Type: GrantFiled: January 12, 1987Date of Patent: December 13, 1988Assignee: Sandoz Ltd.Inventor: Walter Haefliger
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Patent number: 4772709Abstract: Ketoalkyl esters of 1-substituted-6-C.sub.1-4 straight chain alkyl (or allyl)ergoline-8.beta.-carboxylic acid, useful and 5HT receptor antagonists.Type: GrantFiled: October 1, 1985Date of Patent: September 20, 1988Assignee: Eli Lilly and CompanyInventors: Gifford P. Marzoni, William L. Garbrecht
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Patent number: 4772610Abstract: Novel 1-alkyl ergolinylthiourea derivatives of the general formula ##STR1## wherein R.sup.1 is C.sub.1-6 alkyl,R.sup.2 and R.sup.3 are C.sub.1-4 alkyl,R.sup.4 is hydrogen or C.sub.1-4 alkyl andC.sub.9---- C.sub.10 is a single bond or a double bond,and the acid addition salts thereof, with the provision that when R.sup.3 and R.sup.4 are both ethyl, R.sup.1 and R.sup.2 are not methyl and acid addition salts thereof are provided; as well as a process for the preparation of these compounds. The compounds are useful as medicinal agents, e.g., for the treatment of mental depression.Type: GrantFiled: August 6, 1986Date of Patent: September 20, 1988Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Gerhard Sauer, Helmut Wachtel
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Patent number: 4766128Abstract: Substituted ergolines of the formula ##STR1## and their acid addition salts, wherein the urea side chain in the 8-position can be in the d.alpha.- or .beta.-configuration, C.sub.2 C.sub.3 and C.sub.9 C.sub.10 are a CC single or C.dbd.C double bond, andR is hydrogen or NR'R" wherein R'R" is O.sub.2, H.sub.2, C.sub.1-4 -dialkyl, or, together, they form a 3- to 9-membered ring, or R' and R" individually are hydrogen, C.sub.1-4 -alkyl, or C.sub.1-10- -acyl,R.sup.1 is hydrogen, C.sub.1-4 -alkyl, C.sub.1-10 -acyl, C.sub.6-8 -aryl, or C.sub.1-4 -alkylsulfonyl,R.sup.2 is hydrogen or halogen if C.sub.2 C.sub.3 is a C.dbd.C double bond, or hydrogen if C.sub.2 C.sub.3 is a CC single bond,R.sup.6 is C.sub.1-4 -alkyl,show a pronounced effect on the central nervous system and are suitable, for example, as antidepressants, neuroleptics, or antihypertensives.Type: GrantFiled: March 14, 1984Date of Patent: August 23, 1988Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Gregor Haffer, Helmut Wachtel, Herbert H. Schneider, Wolfgang Kehr
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Patent number: 4764517Abstract: A compound of formula I ##STR1## wherein R.sub.1 is n-propyl,R.sub.2 is hydrogen or alkyl(C.sub.1-3),R.sub.3 is alkyl(C.sub.1-3), andR.sub.4 is hydrogen or methylin free base form or in pharmaceutically acceptable acid addition salt form is useful as a prolactin secretion inhibitor, anti-parkinson and anti-depressant agent.Type: GrantFiled: August 25, 1987Date of Patent: August 16, 1988Assignee: Sandoz Ltd.Inventor: Peter Gull
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Patent number: 4753949Abstract: The invention relates to a novel process for the preparation of partially new 2-halonicergoline derivatives of the formula (I), ##STR1## wherein X stands for chlorine, bromine or iodine atom, as well as their acid addition salts.The process of the invention comprises esterifying a novel 2-halo-1-methyllumilysergol of the formula (II), ##STR2## wherein X is the same as defined above, or an acid addition salt thereof and, if desired, converting the thus-obtained 2-halonicergoline derivative of the formula (I) to an acid addition salt.The compounds of the invention improve the cognitive function of the brain and show an antihypoxic as well as a strong .alpha.-adrenerg blocking and calcium-antagonistic action.Type: GrantFiled: June 23, 1986Date of Patent: June 28, 1988Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Gabor Megyeri, Tibor Keve, Bala Stefko, Erik Bogsch, Janos Galambos, Anna Kassi nee Zieger, Ferenc Trischler, Eva Palosi, Dora Groo, Egon Karpati, Zsolt Szombathelyi, Laszlo Szporny, Bela Kiss, Istvan Laszlovszky, Erzsebet Lapis
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Patent number: 4754037Abstract: A process for preparing an N-methyl derivative of ergoline of formula: ##STR1## in which R.sub.1 denotes a carboxy or alkoxycarbonyl group in which the alkyl portion contains 1 to 4 carbon atoms, R.sub.2 denotes a hydrogen atom or a methoxy group and R.sub.3 denotes a hydrogen atom or R.sub.2 and R.sub.3 together form a direct bond, or in which R.sub.1 denotes a hydroxymethyl group, R.sub.2 denotes a hydrogen atom or a methoxy group and R.sub.3 denotes a hydrogen atom, which comprises methylating an ergoline derivative of formula: ##STR2## in which R.sub.1, R.sub.2 and R.sub.3 are defined as above, with methyl carbonate in the presence of a basic agent, in an apolar aprotic solvent in the present of a phase transfer catalyst.Type: GrantFiled: July 10, 1986Date of Patent: June 28, 1988Assignee: Rhone-Poulenc SanteInventor: Christian Gervais
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Patent number: 4748248Abstract: A process for preparing an ergoline of the formula ##STR1## wherein C.sub.9 ----C.sub.10 is a CC single or double bond,R.sup.1 is hydrogen or CONR.sub.2, R being hydrogen, methyl, or ethyl, and wherein NR' is in the .alpha.- or .beta.- position,R.sup.2 is lower alkyl of up to 3 carbon atoms, and the salts thereof,comprises treating the corresponding ergolinyl carboxylic acid amide with lead(IV) acetate in an aprotic polar solvent; reacting the intermediarily formed corresponding isocyanate with water or with a reactive amine of up to 4 carbon atoms, (e.g. a mono- or dialkylamine of up to 4-C atoms); and, optionally, treating the resultant product with an acid to form the corresponding salt.Type: GrantFiled: December 13, 1985Date of Patent: May 31, 1988Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Gregor Haffer
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Patent number: 4746666Abstract: Ergoline derivatives of the formula I ##STR1## wherein R.sub.1 =H,CH.sub.3 ; R.sub.2 =H, halogen, CH.sub.3, CN, C.sub.1 -C.sub.4 alkylthio or phenylthio; R.sub.3 =C.sub.1 -C.sub.4 hydrocarbon; R.sub.4 =H, OCH.sub.3 ; R.sub.5 =H and R.sub.6 =--CH.dbd.CH--CONHR.sub.7 or R.sub.5 and R.sub.6 =.dbd.CH--CONHR.sub.7 ; R.sub.7 =2-thiazolyl, 3-pyridazinyl, 1,3,4-thiadiazol-2-yl or 4-pyrimidinyl group optionally substituted, and pharmaceutically acceptable salts thereof, display activity on the Central Nervous System and are useful as antiprolactinic agents. Their preparation and pharmaceutical compositions containing them are also described.Type: GrantFiled: June 16, 1986Date of Patent: May 24, 1988Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Luigi Bernardi, Sergio Mantegani, Aldemio Temperilli, Gabriella Traquandi, Alessandro Rossi
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Patent number: 4742075Abstract: There are disclosed pharmaceutical compounds of the formula ##STR1## in which R.sup.1 is an aliphatic or aromatic function, and R.sup.2 and R.sup.3 are each hydrogen, C.sub.1-4 alkyl or a protecting group; and salts thereof.Type: GrantFiled: July 22, 1985Date of Patent: May 3, 1988Assignee: Lilly Industries LimitedInventor: William H. Hunter
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Patent number: 4740509Abstract: Novel 12- and 13-bromoergoine derivatives are suitable as medicines for treating psychic disorders of the depressive array of symptoms and also as intermediates.Type: GrantFiled: September 19, 1986Date of Patent: April 26, 1988Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Josef Heindl, Gertrud Schroeder, Helmut Wachtel
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Patent number: 4734501Abstract: The present invention provides a process for N-alkylating dihydrolysergic acid with a substituted benzenesulfonate derivative.Type: GrantFiled: October 1, 1985Date of Patent: March 29, 1988Assignee: Eli Lilly and CompanyInventor: Gifford P. Marzoni
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Patent number: 4731367Abstract: Novel ergoline derivatives, substituted in the 2-position, of the formula ##STR1## wherein C.sub.8 -C.sub.9 and C.sub.9 -C.sub.10 each independently is a CC-single or a C.dbd.C-double bond, but not together a cumulated double bond, and the substituent in the 8-position is in the .alpha.- or .beta.-configuration where C.sub.8 -C.sub.9 is a CC-single bond,R.sup.2 isCN, SR, SOR, ##STR2## wherein n is 2 or 3, ##STR3## and --CH(OH)R, wherein R has the meaning of H or C.sub.1-4 -alkyl, the grouping COR' and CSR' wherein R'.dbd.OH, OC.sub.1-4 -alkyl, benzyl, NH.sub.2 or NHR",the grouping CH.dbd.CH--CO.sub.2 R" and CH.sub.2 --CH.sub.2 --CO.sub.2 R" wherein R".dbd.C.sub.1-4 -alkyl,the grouping C.vertline.C-R'" and HC.dbd.CH--R'" wherein R'".dbd. hydrogen, C.sub.1-4 -alkyl, phenyl, CH.sub.2 OH, CR".sub.2 OH, ##STR4## CO.sub.2 R", CH.sub.2 NR".sub.2 or SiMe.sub.2 R"; C.sub.1-3 -alkyl, or C.sub.1-3 -alkyl substituted by OH or phenyl; or ##STR5## wherein R" is C.sub.1-4 alkyl, R.sup.6 is C.sub.1-4 -alkyl andR.sup.Type: GrantFiled: April 9, 1985Date of Patent: March 15, 1988Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Andreas Huth, Helmut Wachtel, Herbert H. Schneider
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Patent number: 4704395Abstract: Cyclic ether esters of 1-substituted-6-C.sub.1-4 straight chain alkyl (or allyl)ergoline-8.beta.-carboxylic acid, useful as 5HT receptor antagonists.Type: GrantFiled: December 20, 1985Date of Patent: November 3, 1987Assignee: Eli Lilly and CompanyInventors: Gifford P. Marzoni, William L. Garbrecht
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Patent number: 4704396Abstract: Phenacyl or substituted phenacyl esters of 1-substituted-6-C.sub.1-4 straight chain alkyl (or allyl)ergoline-8.beta.-carboxylic acid, useful as 5HT receptor antagonists.Type: GrantFiled: December 20, 1985Date of Patent: November 3, 1987Assignee: Eli Lilly and CompanyInventors: Kathleen R. Whitten, William L. Garbrecht
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Patent number: 4697017Abstract: The invention relates to a novel process for the preparation of 2-bromo-.alpha.-ergocryptine and its acid addition salt by brominating .alpha.-ergocryptine in such a way that the bromination is carried out at room temperature by using a dimethylsulphoxide-hydrogen bromide mixture containing no more 0.02% of water and, if desired, converting the thus-obtained 2-bromo-.alpha.-ergocryptine to an acid addition salt in a known manner.Type: GrantFiled: May 30, 1986Date of Patent: September 29, 1987Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Gabor Megyeri, Tibor Keve, Janos Galambos, Lajos Kovacs, Jr., Bela Stefko, Erik Bogsch, Ferenc Trischler
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Patent number: 4695635Abstract: 2-bromoergolines can be reduced in good yields, without dimerization as determined by NMR product analysis, to the corresponding 2,3-dihydroergolines under otherwise conventional reducing conditions by introducing 2-bromoergolines, together with sodium borohydride, into trifluoroacetic acid under cooling to prevent the reaction mixture from rising above ambient temperature.Type: GrantFiled: March 28, 1985Date of Patent: September 22, 1987Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Gregor Haffer
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Patent number: 4690929Abstract: Compounds of formula I: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 represents a hydrogen or halogen atom or a methyl, cyano, C.sub.1 -C.sub.4 alkylthio or phenylthio group; R.sub.7 and R.sub.8 represent hydrogen atoms and R.sub.3 represents a hydrogen atom or a methoxy group, or R.sub.7 represents a hydrogen atom and R.sub.3 and R.sub.8 taken together represent a bond, or R.sub.3 represents a hydrogen atom or a methoxy group and R.sub.7 and R.sub.8 taken together represent a bond; R.sub.4 represents a hydrocarbon group having from 1 to 4 carbon atoms; R.sub.5 represents a hydrogen atom or a hydrocarbon group having from 1 to 4 carbon atoms or a phenyl group; X represents an oxygen or sulphur atom or an imino group, R.sub.9 represents a hydrogen atom and B represents a cyano, a C.sub.2 -C.sub.5 alkoxycarbonyl or carbamoyl group, or R.sub.Type: GrantFiled: April 26, 1984Date of Patent: September 1, 1987Assignee: Farmitalia Carlo ErbaInventors: Luigi Bernardi, Laura Chiodini, Sergio Mantegani, Daniela Ruggieri, Aldemio Temperilli, Patricia Salvati
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Patent number: 4683237Abstract: Mono, difluoro or trifluoroalkyl esters of 1-substituted-6-C.sub.1-4 straight chain alkyl (or allyl)-ergoline-8.beta.-carboxylic acid, useful as 5HT.sub.2 receptor antagonists.Type: GrantFiled: December 20, 1985Date of Patent: July 28, 1987Assignee: Eli Lilly and CompanyInventors: Gifford P. Marzoni, William L. Garbrecht
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Patent number: 4683236Abstract: Cycloalkyl or ketocycloalkyl esters of 1-substituted-6-C.sub.1-4 straight chain alkyl (or allyl)-ergoline-8.beta.-carboxylic acids, useful as 5HT.sub.2 receptor antagonists.Type: GrantFiled: October 1, 1985Date of Patent: July 28, 1987Assignee: Eli Lilly and CompanyInventors: Kathleen R. Whitten, William L. Garbrecht, Gifford P. Marzoni, C. John Parli
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Patent number: 4515950Abstract: 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: GrantFiled: April 26, 1982Date of Patent: May 7, 1985Assignee: Sandoz Ltd.Inventors: Zdenek Brich, Herbert Muhle
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Patent number: 4500712Abstract: There are provided ergoline derivatives of formula ##STR1## wherein R.sub.1 .dbd.H, CH.sub.3 ; R.sub.2 .dbd.H or halogen atom, or CH.sub.3,CN, alkyl- or phenyl-thio; R.sub.3 .dbd.H, OCH.sub.3 ; R.sub.4 .dbd.C.sub.1 -C.sub.4 hydrocarbon group; X.dbd.O, S, NH; A.dbd.CO, SO.sub.2 ; B.dbd.C.sub.1 -C.sub.4 hydrocarbon group, aryl, aralkyl, heterocyclic ring group, alkoxy, aryloxy; n.dbd.0, 1, 2; and pharmaceutically acceptable salts thereof.A process for preparing said compounds is also provided. The compounds show anti-hypertensive activity and are active on the gastroenteric system.Type: GrantFiled: November 1, 1982Date of Patent: February 19, 1985Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Luigi Bernardi, Aldemio Temperilli, Daniela Ruggieri, Giuliana Arcari, Patricia Salvati
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Patent number: 4491664Abstract: 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: GrantFiled: March 12, 1982Date of Patent: January 1, 1985Assignee: Sandoz Ltd.Inventor: Wolfgang Oppolzer
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Patent number: 4417051Abstract: 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: GrantFiled: May 12, 1981Date of Patent: November 22, 1983Assignee: Schering, AktiengesellschaftInventor: Gerhard Sauer
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Patent number: 4382800Abstract: Soluble polymeric colorants composed of free amine groups and chromophoric groups covalently bonded to an organic backbone are disclosed. The number of free amine groups is not less than one-half the number of chromophoric groups. The colorants are characterized by being free of sulfonate, phosphonate and carboxylate groups. The preparation and use of these colorants is also disclosed.Type: GrantFiled: September 28, 1981Date of Patent: May 10, 1983Assignee: DynapolInventors: Patricia C. Wang, Robert E. Wingard, Jr.
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Patent number: 4379790Abstract: Compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein R.sub.1 is alkyl of 2-6 carbon atoms, ##STR2## n is 1, or 2, m is 0 or 1,R.sub.2 is alkyl of 1-6 carbon atoms, ##STR3## is a CC single bond or a CC double bond, and the 8-positioned urea residue can be in the .alpha.- or .beta.-position, have valuable pharmacological properties, e.g., lactation inhibition and anti-Parkinsonism.Type: GrantFiled: January 6, 1982Date of Patent: April 12, 1983Assignee: Schering AktiengesellschaftInventors: Reinhard Horowski, Wolfgang Kehr, Gerhard Sauer, Ulrich Eder, Hans P. Lorenz
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Patent number: 4348391Abstract: The present invention provides compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine,R.sub.1 is methyl or ethyl,R.sub.2 is alkyl of 1 to 4 carbon atoms or allyl,R.sub.3 is CH.sub.2 CN or a group --NR.sub.4 R.sub.5, wherein R.sub.4 is hydrogen or alkyl of 1 to 4 carbon atoms, and R.sub.5 is alkanoyl of 1 to 5 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms in the aggregate thereof, or mono-, di- or tri-haloalkoxycarbonyl of 3 to 5 carbon atoms, wherein the alkoxy group is substituted by halogen other than in the .alpha. position to the oxygen atom, or R.sub.5 is SO.sub.2 R.sub.6, wherein R.sub.6 is alkyl of 1 to 4 carbon atoms, mono-, di- or tri-haloalkyl of 1 to 4 carbon atoms, phenyl, phenyl mono-substituted by halogen or alkoxy of 1 to 4 carbon atoms, or pyridyl, or R.sub.6 is a group NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are, independently, hydrogen or alkyl of 1 to 4 carbon atoms, or R.sub.7 and R.sub.8 together form --[CH.sub.2 ].sub.n -- or --[CH.sub.2 ].sub.2 --A--[CH.Type: GrantFiled: September 22, 1980Date of Patent: September 7, 1982Assignee: Sandoz Ltd.Inventors: Peter Stutz, Theodor Fehr, Paul Stadler
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Patent number: 4348392Abstract: This invention provides new compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine,R.sub.1 is methyl or ethyl, andR.sub.2 is CH.sub.2 --CN, or a group NR.sub.3 R.sub.4, whereinR.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms, andR.sub.4 is SO.sub.2 R.sub.5, wherein R.sub.5 is alkyl of 1 to 4 carbon atoms, mono- to tri-halogenalkyl of 1 to 4 carbon atoms, phenyl, pyridyl, phenyl monosubstituted by halogen or alkoxy of 1 to 4 carbon atoms, or a group NR.sub.6 R.sub.7, wherein each ofR.sub.6 and R.sub.7 is independently hydrogen or alkyl of 1 to 4 carbon atoms, orR.sub.6 and R.sub.7 together are one of the groups (CH.sub.2).sub.n or (CH.sub.2).sub.2 --A--(CH.sub.2).sub.2, whereinn is a number from 3 to 7, andA is oxygen, sulphur or nitrogen substituted by alkyl of 1 to 4 carbon atoms or phenyl,useful as prolactin secretion agents and antiparkinson agents.Type: GrantFiled: September 22, 1980Date of Patent: September 7, 1982Assignee: Sandoz Ltd.Inventors: Theodor Fehr, Paul Stadler, Peter Stutz
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Patent number: 4321381Abstract: Compounds and process for making same are disclosed, the compounds having the formula (I): ##STR1## wherein R.sub.1 represents methyl, phenyl, piperidino, 1-pyrrolidinyl, morpholino or 4-methyl-1-piperazinyl, alkyl or alkoxy having from 1 to 4 carbon atoms, amino, substituted amino of the formula NHR' (wherein R' is alkyl having from 1 to 4 carbon atoms, cycloalkyl, a benzyl, or phenyl) or substituted amino of the formula NR" R"' (wherein R" and R"' both represent alkyl having from 1 to 4 carbon atoms);R.sub.2 represents a hydrogen atom, alkyl having from 1 to 4 carbon atoms, or phenyl;R.sub.3 represents a fluorine atom, cyano, difluoromethyl, difluorobromomethyl, trifluoromethyl, methylthio, methylsulphonyl, sulphonamido, an alkoxy having from 1 to 4 carbon atoms, an alkanoyl having from 2 to 5 carbon atoms, or benzoyl;R.sub.4 represents a hydrocarbon having from 1 to 4 carbon atoms;R.sub.5 represents a hydrogen atom or methoxy;R.sub.6 represents a hydrogen or halogen atom or methyl; andR.sub.Type: GrantFiled: September 19, 1980Date of Patent: March 23, 1982Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Sergio Mantegani, Guiliana Arcari, Anna M. Caravaggi, Germano Bosisio
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Patent number: 4321198Abstract: Novel compositions comprising acetylenic polyhemi-amic acid compositions and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal .dbd.C.tbd.CH groups as hemi-amic acid groups of their derivatives. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.Type: GrantFiled: January 25, 1980Date of Patent: March 23, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, Phillip A. Waitkus
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Patent number: 4316844Abstract: Novel compositions comprising unsaturated polyhemi-amic acid compositions and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide unsaturated amide groups having terminal --CH.dbd.CH.sub.2 groups as hemi-amic acid groups or their derivatives. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.Type: GrantFiled: January 25, 1980Date of Patent: February 23, 1982Assignee: Plastics Engineering CompanyInventors: Phillip A. Waitkus, Gaetano F. D'Alelio
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Patent number: 4316845Abstract: Novel compositions comprising acetylenic polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal --C.dbd.CH groups. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.Type: GrantFiled: January 25, 1980Date of Patent: February 23, 1982Assignee: Plastics Engineering CompanyInventors: Gaetano F. D'Alelio, Phillip A. Waitkus
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Patent number: 4316843Abstract: Novel compositions comprising unsaturated polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide unsaturated amide groups having terminal --CH.dbd.CH.sub.2 groups. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.Type: GrantFiled: January 25, 1980Date of Patent: February 23, 1982Assignee: Plastics Engineering CompanyInventors: Phillip A. Waitkus, Gaetano F. D'Alelio
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Patent number: 4245095Abstract: Isoquinoline compounds of the following formula are described: ##STR1## wherein the moiety A-B represents a group of formula:--CH.sub.2 --NR.sup.3 -- or --NR.sup.3 --CH.sub.2 --;wherein R.sup.3 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl C.sub.3-6 cycloalkyl-C.sub.1-4 alkyl, optionally substituted benzyl, C.sub.3-6 alkenyl or C.sub.1-4 alkanoyl;wherein R represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, or optionally substituted benzyl;wherein R.sup.1 and R.sup.2 each represent hydrogen or taken together represent a chemical bond; and wherein X is hydrogen or halogen; or an acid-addition salt thereof.The compounds are pharmaceuticals and especially useful in the treatment of disorders of the central nervous system.Type: GrantFiled: February 1, 1980Date of Patent: January 13, 1981Assignee: Lilly Industries LimitedInventors: David C. Horwell, David E. Tupper
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Patent number: 4237291Abstract: 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: GrantFiled: December 20, 1978Date of Patent: December 2, 1980Assignee: VEB Arzneimittelwerk DresdenInventors: Werner Grawert, Ludwig Schiedt, Brigitte Neumann, Karlheinz Heidenbluth, Christoph Dauth, Rudolf Schirutschke, Monika Muller
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Patent number: 4232157Abstract: A novel process is disclosed for the preparation of derivatives of lysergol having the general formula: ##STR1## According to this process lysergol is directly used as the starting compound and, after the methylation at the 1 position of the corresponding 10 alpha-methoxy-lumilysergol, the methylated compound is directly esterified with a carboxylic acid R--COOH, the acid being selected in the group comprising aliphatic, cycloaliphatic, aromatic, and heterocyclic carboxylic acids, containing up to 10 carbon atoms.Type: GrantFiled: April 3, 1979Date of Patent: November 4, 1980Inventor: Corvi M. Enrico
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Patent number: 4231921Abstract: Novel compounds of the general formula I ##STR1## wherein M.sup.q.sym. is a metal ion carrying a double or triple positive charge and q is 2 or 3 and r is 1 or 2, the quotient q/r being 1, 1.5, 2 or 3, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions, and m is 0, 1 or 2 and A is H.sub.2 O or an amine.Type: GrantFiled: July 10, 1978Date of Patent: November 4, 1980Assignee: Ciba-Geigy CorporationInventor: Paul Moser
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Patent number: RE31194Abstract: Isoquinoline compounds of the following formula are described: ##STR1## wherein the moiety A-B represents a group of formula:--CH.sub.2 --NR.sup.3 -- or --NR.sup.3 --CH.sub.2 --;wherein R.sup.3 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl C.sub.3-6 cycloalkyl-C.sub.1-4 alkyl, optionally substituted benzyl, C.sub.3-6 alkenyl or C.sub.1-4 alkanoyl;wherein R represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, or optionally substituted benzyl;wherein R.sup.1 and R.sup.2 each represent hydrogen or taken together represent a chemical bond; and wherein X is hydrogen or halogen; or an acid-addition salt thereof.The compounds are pharmaceuticals and especially useful in the treatment of disorders of the central nervous system.Type: GrantFiled: August 17, 1981Date of Patent: March 29, 1983Assignee: Lilly Industries, LimitedInventors: David C. Horwell, David E. Tupper