Abstract: 3-Fluoro-2,3-dihydro-1H-1,4-benzodiazepin-2-ones of the formula ##STR1## wherein R.sup.1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R.sup.2 is phenyl; monohalophenyl or pyridyl; R.sup.3 is F, Cl, Br or NO.sub.2, and physiologically acceptable acid addition salts thereof, are central nervous system depressants.
Type:
Grant
Filed:
December 9, 1975
Date of Patent:
November 4, 1980
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Abstract: 2-Acyl-4-oxo-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives of the formula ##STR1## wherein COR is the acyl radical of an up to 26 carbon atom acid and their physiologically acceptable acid addition and quaternary ammonium salts, are anthelmintics and can be produced by reacting 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline with an acid or a reactive functional derivative thereof. This is a division, or application Ser. No. 742,133, filed on Nov. 15, 1976, which in turn is a divisional of Ser. No. 533,467, filed on Dec. 16, 1974, now U.S. Pat. No. 4,001,411.
Type:
Grant
Filed:
December 18, 1978
Date of Patent:
April 1, 1980
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Jurgen Seubert, Herbert Thomas, Peter Andrews
Abstract: Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologically acceptable metals salts thereof, have anti-inflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.
Type:
Grant
Filed:
June 28, 1978
Date of Patent:
April 1, 1980
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
Abstract: Compounds of the formula (I) ##STR1## wherein X is --R, --OR or --O--CO--R and R is alkyl of 1-12 C-atoms, are useful as liquid crystals or as solvents for measuring n.m.r., u.v. or visible spectra in anisotropic media.
Type:
Grant
Filed:
January 11, 1978
Date of Patent:
January 1, 1980
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Rudolf Eidenschink, Joachim Krause, Ludwig Pohl
Abstract: Novel liquid crystals have the formula ##STR1## wherein two of the rings A, B and C are aromatic and the third is a trans-1,4-disubstituted cyclohexane ring and R is alkyl or alkoxy each of 1 - 12 C-atoms. These compounds are particularly useful as additional components in liquid crystal dielectrics whereby the clear point of the dielectric is raised and the viscosity thereof is not deleteriously affected.
Type:
Grant
Filed:
January 11, 1978
Date of Patent:
May 15, 1979
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Rudolf Eidenschink, Joachim Krause, Ludwig Pohl
Abstract: Isoquinolines of the formula ##STR1## wherein R.sup.1 is H or alkyl of 1 - 4 carbon atoms, R.sup.2 is H and R.sup.3 is OH or R.sup.2 and R.sup.3 collectively are a C--C bond, and physiologically acceptable acid addition salts thereof have anti-depressant activity and can be prepared by solvolyzing or hydrogenolyzing a compound of the formula ##STR2## or an acid addition salt thereof, wherein R.sup.4 is R.sup.1 or R.sup.6, R.sup.5 is OR.sup.7 or, when R.sup.4 is R.sup.6, R.sup.3 ; R.sup.6 and R.sup.7 are radicals which can be split off solvolytically or hydrogenolytically and R.sup.1 and R.sup.2 are as above; and the optional step of dehydrating a resulting carbinol (R.sup.2 is H, R.sup.3 is OH) and/or treating a resulting compound (R.sup.1 is H) with a N-alkylating agent and/or converting a resulting base to a physiologically acceptable acid addition salt by treatment with and acid.
Type:
Grant
Filed:
June 13, 1977
Date of Patent:
October 24, 1978
Assignee:
Merck Patent Gesellschaft mit Beschraenkter Haftung
Inventors:
Rolf Pohlke, Wighard Strehlow, Helmut Mueller-Calgan, Christoph Seyfried
Abstract: Compounds of the formulaR--A--Zwherein R is 4-biphenylyl or 4-phenoxyphenyl or a corresponding group monosubstituted or polysubstituted by one or more of F, Cl and Br; A is --CH(CH.sub.3)--CH.sub.2 --(CH.sub.2).sub.n --, --C(CH.sub.3).dbd.CH--(CH.sub.2).sub.n -- or --C(OH) (CH.sub.3)--CH.sub.2 --(CH.sub.2).sub.n --; Z is --NR.sup.1 R.sup.2, imidazol-1-yl, phthalimido or 4,5-dihydro-4-oxophthalazin-1-yl-amino; R.sup.1 and R.sup.2 each are H or alkyl, azaalkyl or acyl, each of 1 - 6 carbon atoms or, collectively, are alkylene of 4 - 7 carbon atoms, 3-oxapentamethylene or 3-R.sup.3 -3-azapentamethylene; R.sup.3 is H or alkyl or hydroxyalkyl each of up to 6 carbon atoms; and n is 0, 1 or 2, and their physiologically acceptable acid addition salts possess anti-inflammatory, anti-arteriosclerotic and serum cholesterol and triglyceride level lowering activities.
Type:
Grant
Filed:
October 22, 1975
Date of Patent:
August 29, 1978
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Joachim Gante, Hans-Adolf Kurmeier, Erich Schacht, Werner Mehrhof, Dieter Orth, Albrecht Wild, Zdenek Simane
Abstract: Novel indoline derivatives of the formula ##STR1## wherein R is H or CH.sub.3 O and the X each are Cl or Br or collectively are --N(CH.sub.2 C.sub.6 H.sub.5)-- or acid addition salts thereof are obtained by treating a 3-hydroxy-1,2,3,4-tetrahydroquinoline of the formula ##STR2## with an inorganic acid halide and, if appropriate, the reacting resulting dihalogen compound with benzylamine or converting a resulting acid addition salt by treatment with a base in the free base or converting a free base by treatment with an acid to an acid addition salt.
Type:
Grant
Filed:
January 30, 1976
Date of Patent:
January 24, 1978
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Abstract: A separating material for thin layer chromatography comprising an inert substrate coated with a sorption agent consisting essentially of silica gel particles about 3 to 8 .mu.m in diameter in a layer 100-300 .mu.m thick.
Type:
Grant
Filed:
May 27, 1976
Date of Patent:
December 20, 1977
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Herbert Halpaap, Walter Reich, Johannes Ripphahn
Abstract: Lustrous pigments based on mica flakes coated with metal oxides have a very uniform coating layer of tin dioxide, which can contain aluminum oxide, or the hydrates thereof.
Type:
Grant
Filed:
May 18, 1976
Date of Patent:
August 9, 1977
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Abstract: Organic solvents containing less than 0.2 atom percent of .sup.13 C and which preferably are at least partially deuterated are produced from .sup.13 C-depleted gaseous carbon compounds and are advantageously employed as solvents for .sup.13 C NMR spectroscopy.
Type:
Grant
Filed:
October 26, 1973
Date of Patent:
May 4, 1976
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Ludwig Pohl, Werner Theysohn, Richard Unger
Abstract: Improved allergen-containing extracts are obtained by the extraction of allergy-causing materials, such as pollen and house dust, with hydrophilic aqueous extractants, by pretreating the allergen-containing material with a lipophilic, aqueous extraction liquid. Allergens extracted in the two steps can be combined and formed into allergen preparations, which can be used both for diagnostic and therapeutic purposes.
Type:
Grant
Filed:
December 5, 1973
Date of Patent:
April 27, 1976
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung
Inventors:
Otto Nieschulz, Gunther Rudiger, Jurgen Maas
Abstract: Nematic esters of the formula ##SPC1##Wherein R.sub.1 and R.sub.2 are each alkyl, alkoxyalkyl, alkoxy or alkoxyalkoxy of 1 to 10 carbon atoms, X is CN or NO.sub.2 and Y is H or X which are useful for influencing the electrooptic properties of other nematic compositions.
Type:
Grant
Filed:
December 18, 1974
Date of Patent:
April 27, 1976
Assignee:
Merck Patent Gesellschaft mit beschraenkter Haftung