Abstract: The present invention relates to a new crystalline modification of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,S-dihydro-1H-pyrrolizin-S-ylacetic acid which is referred to as polymorph B. It has a peak in the solid state 13C-NMR spectrum (with adamantane as external reference standard; CH group d=29.45 ppm) in the range from 179.8 to 180.2 ppm and can be processed directly to a pharmaceutical formulation.
Type:
Grant
Filed:
March 20, 2006
Date of Patent:
October 11, 2011
Assignee:
Merckle GmbH
Inventors:
Wolfgang Albrecht, Thomas Kammermeier, Hans-Gunter Striegel, Philipp Merckle, Stefan Laufer
Abstract: The invention relates to novel heteroaryl substituted acetone derivatives which inhibit the enzyme phospholipase A2, pharmaceutical preparations containing these compounds and a method of producing these compounds.
Abstract: The present invention relates to compounds of the formula I in which R1, R2, R3, R4, X and Y have the meanings indicated in the description. These compounds have immunomodulating effects, as well as an inhibiting or regulating effect on the release of IL-1? and/or TNF-?. They can therefore be used for the treatment of diseases associated with a disturbance of the immune system.
Type:
Application
Filed:
May 12, 2006
Publication date:
April 23, 2009
Applicant:
Merckle GMBH
Inventors:
Stefan Laufer, Wolfgang Albrecht, Cornelia Greim, Hans-Guenter Striegel, Karola Tollmann
Abstract: The invention relates to 2-thio-substituted imidazole derivatives of the formula I in which the radicals R1, R2, R3, R4 and p are as defined in the description. The compounds according to the invention have immunomodulating and/or cytokine-release-inhibiting action and are therefore suitable for treating disorders associated with a disturbed immune system.
Type:
Grant
Filed:
May 16, 2003
Date of Patent:
October 28, 2008
Assignee:
Merckle GmbH
Inventors:
Stefan Laufer, Hans-Guenter Striegel, Wolfgang Albrecht, Karola Tollmann
Abstract: Treating or preventing degeneration or destruction of articular cartilage and/or subchondral bone in the affected joint of a mammal is accomplished by administering a compound of formula (I), wherein the variables have the meanings given in the present description. A preferred compound of formula (I) is formula (II).
Abstract: This invention features a compound of the following formula: wherein T is a transportophore, L is a bond or linker, and C is an antibiotic therapeutic agent, the transportophore is covalently bonded to the antibiotic therapeutic agent via the bond or the linker, and the transportophore is an azithromycin derivative or crown ether derivative.
Type:
Grant
Filed:
February 14, 2003
Date of Patent:
September 18, 2007
Assignee:
Merckle GmbH
Inventors:
Michael Burnet, Jan-Hinrich Guse, Gene Kim
Abstract: The invention relates to 2-thio-substituted imidazole derivatives of the formula I in which the radicals R1, R2, R3 and R4 are as defined in the description. The compounds according to the invention have immunomodulating and/or cytokine-release-inhibiting action and are therefore suitable for treating disorders associated with a disturbed immune system.
Type:
Grant
Filed:
February 19, 2002
Date of Patent:
August 7, 2007
Assignee:
Merckle GmbH
Inventors:
Stefan Laufer, Dunja Kotschenreuther, Philipp Merckle, Karola Tollmann, Hans-Guenter Striegel
Abstract: The invention relates to a process for the preparation of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-ylacetic acid, in which 5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole is reacted with ?-bromo-4-chloroacetophenone with formation of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine and the acetic acid group is introduced into the 5-position, 5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole being obtained by hydrogenation of 2,2-dimethyl-4-oxo-5-phenylvaleronitrile or a ketal thereof. The invention also relates to processes for the preparation of intermediates occurring in the above process.
Type:
Grant
Filed:
August 21, 2002
Date of Patent:
July 18, 2006
Assignee:
Merckle GmbH
Inventors:
Gerd Dannhardt, Thomas Kammermeier, Philipp Merckle, Hans-Günter Striegel, Stefan Laufer
Abstract: The present invention relates to fused pyrrole compounds of the formula 1. in which at least one of the radicals R1, R2, R3 is 4-sulphur-substituted phenyl. These compounds are in particular pyrrolizines, indolizines and heteroanalogues having selective inhibitory action on isoenzyme-2 of prostaglandin H synthase (COX-2). The invention also relates to pharmaceutical compositions which contain these compounds; and the use of these compounds for the treatment of disorders of the rheumatic type.
Type:
Grant
Filed:
January 12, 2001
Date of Patent:
August 30, 2005
Assignee:
Merckle GmbH
Inventors:
Hans-Guenter Striegel, Stefan Laufer, Karola Tollmann, Susanne Tries
Abstract: The present invention relates to the use of tissue factor for influencing blood vessel formation, particularly for activating blood vessel formation, above all for wound healing.
Type:
Grant
Filed:
May 8, 1998
Date of Patent:
August 16, 2005
Assignee:
Merckle GmbH
Inventors:
Peter Nawroth, Katsumi Nakagawa, Youming Zhang
Abstract: The present invention relates to compounds of the formula I in which one of the radicals R8 and R9 is a hydrogen atom or an alkyl group and the other is hydroxyl, alkoxy or acyloxy or where R8 and R9, together with the carbon atom to which they are bonded, are a carbonyl group and the radicals R1 to R7 have the meanings indicated in the description. The compounds inhibit the release of various mediators of the arachidonic acid cascade and can thus be used for the prevention of allergically induced disorders or for the treatment of disorders of the rheumatic type.
Type:
Grant
Filed:
November 23, 1999
Date of Patent:
April 12, 2005
Assignee:
Merckle GmbH
Inventors:
Stefan Laufer, Karola Tollmann, Hans-Guenter Striegel
Abstract: The present invention relates to 4-pyridyl- and 2,4-pyrimidinyl-substituted pyrrole derivatives and their use in pharmacy, of the formula 1: in which the variables have the meanings indicated in the description. The compounds according to the invention have immunomodulating and/or cytokine release-inhibiting action and are therefore utilizable for the treatment of disorders which are connected with a disturbance of the immune system.
Type:
Grant
Filed:
January 31, 2001
Date of Patent:
March 15, 2005
Assignee:
Merckle GmbH
Inventors:
Hans-Guenter Striegel, Stefan Laufer, Karola Tollmann, Susanne Tries
Abstract: The invention relates to the utilization of monocytes growth factor CD137 or of a functional analogue thereof in order to produce a medicament for promoting the proliferation of peripheral monocytes of a mammal. The invention especially relates to the utilization of the growth factor for treating pathological conditions.
Abstract: The invention relates to a device and to a process for the automatic synthesis of macromolecules on a tape-like substrate material (11). The device has at least one synthesis module (12) which can be sealed from the outside and comprises reaction chambers (15) and fluid lines (18, 19) for filling and emptying the reaction chambers (15) with and of reaction media, it being possible to introduce the substrate material (11) into the synthesis module (12) and bring it into contact with the reaction chambers (15). Transport means (20-26) which are intended to move the substrate material (11) through a particular distance and can be actuated by a control device are furthermore provided. The invention also relates to the use of such a device for the synthesis of oligonucleotides bound on a functionalized substrate material, in particular the production of oligonucleotide libraries.
Type:
Grant
Filed:
November 8, 1999
Date of Patent:
April 8, 2003
Assignee:
Merckle GmbH
Inventors:
Hermann Brugger, Christian Rembe, Raoul Bader, Eberhard P. Hofer, Hartmut Seliger
Abstract: The invention relates to a microactuator arranged on a thermally insulating layer (2) and having a resistance layer (4) made from doped diamond, which is provided with an electrical supply and an electrical leakage (9).
Type:
Grant
Filed:
December 4, 2001
Date of Patent:
January 14, 2003
Assignee:
Merckle GmbH
Inventors:
Eberhard P. Hofer, Erhard Kohn, Christian Rembe, Stefan Aus Der Wiesche, Peter Gluche, Rudiger Leuner
Abstract: The invention relates to 4-heteroaryl-5-phenylimidazole derivatives having 2-arylalkylthio, 2-arylalkenylthio and 2-arylalkynylthio substitution, of the general formula I:
in which Ar is a phenyl radical, Het is a hetero aromatic radical, A is an alkylene chain, R1 is an alkylthio, alkylsulfinyl, alkylsulfonyl, sulfonamido or alkylcarbonyl group and R2 is an alkyl, hydroxyl, alkoxy, alkoxycarbonyl, sulfonamido, carboxyl, nitro or aminocarbonyl group or a halogen atom. n can be 1 or 2 and m is 0 to 2. The compounds according to the invention show antiinflammatory activity.
Type:
Grant
Filed:
May 11, 2001
Date of Patent:
August 13, 2002
Assignee:
Merckle GmbH
Inventors:
Stefan Laufer, Hans-Günter Striegel, Karola Neher
Abstract: The present invention relates to a process process for the preparation of the compound of the formula I
where the compound of the formula III
is reacted with oxalyl chloride and the product obtained is treated with hydrazine and an alkali metal hydroxide in the aqueous phase at elevated temperature, after treatment is complete a three-phase system is produced by addition of an ether and the compound of the formula I is obtained by acidifying the middle phase.
The invention moreover relates to a polymorph of the compound of the formula I.
Type:
Grant
Filed:
January 26, 2001
Date of Patent:
July 9, 2002
Assignee:
Merckle GmbH
Inventors:
Thomas Kammermeier, Stefan Laufer, Philipp Merckle, Hans-Guenter Striegel
Abstract: The invention provides novel antiinflammatory and analgesic agents of the formulae
The novel compounds have an improved inhibitory effect and/or less cytotoxicity in comparison with compounds known from the prior art. The compounds according to the invention are outstandingly suitable for preventing and/or treating disorders caused or partly caused by an increased activity of the enzyme phospholipase A2, such as, for example, inflammations, allergies, asthma, psoriasis and endotoxic shock.
Abstract: The present invention relates to heterocyclic compounds of the formula ##STR1## in which R.sup.1 -R.sup.7, B, a and X have the meanings recited in the specification. These compounds are usable in the treatment of diseases of the rheumatoid variety and for the prevention of allergically induced diseases.
Type:
Grant
Filed:
March 28, 1996
Date of Patent:
September 28, 1999
Assignee:
Merckle GmbH
Inventors:
Stefan Laufer, Hans Gunther Striegel, Gerd Dannhardt