Patents Assigned to Speedel Pharma AG
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Patent number: 7402587Abstract: Crystalline forms A and B of 5-methyl-pyridine-2-sulfonic acid [6-methoxy-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide of formula (I) are described, whereby form B is the most stable form. 5-methyl-pyridine-2-sulfonic acid [6-methoxy-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide also forms solvates with, for example, ethanol, acetone, tetrahydrofuran, methanol, isopropanol, 2-butanone and dichloromethane.Type: GrantFiled: May 12, 2005Date of Patent: July 22, 2008Assignee: Speedel Pharma AGInventors: Thierry Briand, Alexander Bilz, Fritz Blatter, Martin Szelagiewicz
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Patent number: 7153675Abstract: A process for the preparation of 2(S)-alkyl-5-halogenpent-4-ene carboxylic esters by enzymatic hydrolysis, comprising the steps: a) enzymatic hydrolysis of racemic 2-alkyl-5-halogenpent-4-ene carboxylic esters in aqueous and alkaline medium in the presence of an esterase; b) isolation of 2(S)alkyl-5-halogenpent-4-ene carboxylic esters by extraction with an organic solvent; c) isolation of 2(R)-alkyl-5-halogenpent-4-ene carboxylic acids from the aqueous-alkaline medium; d) Esterification of 2(R)-alkyl-5-halogenpent-4-ene carboxylic acids, e) subsequent racemization to form 2-alkyl-5-halogenpent-4-ene carboxylic esters; and f) return of the racemate obtained in step e) to step a), if necessary together with fresh racemic 2-alkyl-5-halogenpent-4-ene carboxylic esters. The process permits the undesired R-stereoisomers to be converted into the desired 2(S)-alkyl-5-halogenpent-4-ene carboxylic esters to avoid waste product from the synthesis.Type: GrantFiled: April 26, 2002Date of Patent: December 26, 2006Assignee: Speedel Pharma AGInventors: Peter Herold, Stefan Stutz
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Patent number: 7132569Abstract: From compounds of formula II wherein R1 and R2 are independently of one another H, C1–C6alkyl, C1–C6halogenalkyl, C1–C6alkoxy, C1–C6alkoxy-C1–C6alkyl, or C1–C6alkoxy-C1–C6alkyloxy, R3 is C1–C6alkyl, R4 is C1–C6alkyl, and R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6-alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6-alkyl, C1–C6-dialkylamino-C1–C6-alkyl, C1–C6-alkanoylamido-C1–C6-alkyl, HO(O)C—C1–C6-alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2N—C(O)—C1–C6-alkyl, R6 is C1–C6alkyl, R7 is C1–C6alkyl or C1–C6alkoxy, or R6 and R7 together are tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or —CH2CH2O— substituted, if necessary, with C1–C4-Alkyl, phenyl or benzyl, it is possible—through halolactonization, azidation of the halogen group, ring opening with an amine R5—NH2, and reduction of the azide group to form the amino group—to prepare compounds of formula I wherein R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6Type: GrantFiled: October 21, 2005Date of Patent: November 7, 2006Assignee: Speedel Pharma AGInventors: Peter Herold, Stefan Stutz, Adriano Indolese
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Patent number: 7009078Abstract: From compounds of formula II wherein R1 and R2 are independently of one another H, C1–C6alkyl, C1–C6halogenalkyl, C1–C6alkoxy, C1–C6alkoxy-C1–C6alkyl, or C1–C6alkoxy-C1–C6alkyloxy, R3 is C1–C6alkyl, R4 is C1–C6alkyl, and R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6-alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6-alkyl, C1–C6-dialkylamino-C1–C6-alkyl, C1–C6-alkanoylamido-C1–C6-alkyl, HO(O)C—C1–C6-alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2N—C(O)—C1–C6-alkyl, R6 is C1–C6alkyl, R7 is C1–C6alkyl or C1–C6alkoxy, or R6 and R7 together are tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or —CH2CH2O— substituted, if necessary, with C1–C4-Alkyl, phenyl or benzyl, it is possible—through halolactonization, azidation of the halogen group, ring opening with an amine R5—NH2, and reduction of the azide group to form the amino group—to prepare compounds of formula I wherein R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6aType: GrantFiled: July 13, 2000Date of Patent: March 7, 2006Assignee: Speedel Pharma AGInventors: Peter Herold, Stefan Stutz, Adriano Indolese
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Patent number: 6881868Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).Type: GrantFiled: June 26, 2001Date of Patent: April 19, 2005Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
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Patent number: 6800769Abstract: Compounds of formula (XII), are simultaneously halogenated in the 5 position and hydroxylated in the 4 position under lactonization, the halolactone is reacted with an amine to form a carboxamide, the halogen is replaced with azide, if necessary after the introduction of a hydroxy protecting group, the resulting azide is converted to a lactone, the lactone is amidated and then the azide converted to the amine group, in order to obtain compounds of formula (I) or a salt thereof.Type: GrantFiled: January 24, 2003Date of Patent: October 5, 2004Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold
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Patent number: 6777574Abstract: Compounds of formula I in the form of their racemates or enantiomers, preferably compounds of formula Ia wherein R4 is C1-C6alkyl, Z is chlorine, bromine or iodine, and X is —OH, chloride, bromide or iodide, or X forms an ester group with the carbonyl substituent, as well as salts of carboxylic acids. The compounds are valuable intermediates for the propagation of &dgr;-amino-&ggr;-hydroxy-&ohgr;-aryl-alkanecarboxamides, which exhibit renin-inhibiting properties and could be used as antihypertensive agents in pharmaceutical preparations.Type: GrantFiled: January 29, 2002Date of Patent: August 17, 2004Assignee: Speedel Pharma AGInventors: Peter Herold, Stefan Stutz
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Patent number: 6730798Abstract: Compounds of formula (II) are simultaneously halogenated in the 5 position and hydroxylated in the 4 position under lactonization, the halolactone is converted into a hydroxylactone and then the hydroxy group into a leaving group, the leaving group is replaced with azide, the lactone amidated and then the azide converted to the amine group, in order to obtain compounds of formula (I).Type: GrantFiled: January 3, 2003Date of Patent: May 4, 2004Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler
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Patent number: 6683206Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1l-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yields by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leavaing group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and their hydrolysis to form corresponding propenic carboxylic acids and their enantioselective hydrogenation, wherein R is (a).Type: GrantFiled: January 2, 2003Date of Patent: January 27, 2004Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
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Patent number: 6670507Abstract: Compounds of formula I wherein R1 is for example 3-methoxyprop-3-yloxy, R2 is for example methoxy, R3 and R4 are in each case for example isopropyl, and R5 is H2NC(O)—[C(CH3)2]—CH2—, are obtainable by reaction of compounds of formula IV with a metal organic derivative of 1-(3-R1-4-R2-phen-1-yl)-2-R3-3-halogen propanes to form a compound of formula VI, followed by removal of the pseudoephedrine protecting group and the OH group, reaction of the resulting lactone with an amine R5—NH2 and removal of protecting group Z.Type: GrantFiled: January 15, 2003Date of Patent: December 30, 2003Assignee: Speedel Pharma AGInventors: Daniel Bellus, Alessandro Dondoni