Patents Assigned to Ragactives, S.L.
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Publication number: 20120004426Abstract: Olopatadine can be obtained by means of a process comprising hydrolysis of a compound of general formula (II), wherein Y is OR1, wherein R1 is C1-C7 alkyl, C3-C7 cycloalkyl, aryl, arylalkyl, or heterocycle; or NR2R3, wherein R2 and R3, independently from each other, are C1-C7 alkyl, aryl, arylalkyl, or R2 and R3 together with the nitrogen atom to which they are bound form a heterocycle of 3 to 7 members, obtained by means of a process comprising reacting the corresponding ester or amide of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid with a suitable Wittig reagent, in the presence of a base in a reaction medium comprising an organic solvent.Type: ApplicationFiled: July 14, 2009Publication date: January 5, 2012Applicant: RAGACTIVES, S.L.U.Inventors: Luis Octavio Silva Guisasola, Lydia Mateos Burón, Antonio Lorente Bonde-Larsen, Luis Gerardo Gutiérrez Fuentes
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Patent number: 7875750Abstract: The present invention relates to a process for preparing 2-amino-6-alkyl-amino-4,5,6,7-tetrahydrobenzothiazoles (I) wherein the asterisk (*) represents an asymmetric carbon and R1 is C1-C6 alkyl; their enantiomers or mixtures thereof, their solvates, hydrates or pharmaceutically acceptable salts, comprising: (a) reacting a compound (II) with a secondary amine, optionally in the presence of an acid and a solvent 1, to form an enamine; (b) optionally removing said acid and said solvent 1, and then reacting said enamine with sulfur in the presence of a solvent 2; and (c) reacting the previously obtained compound with cyanamide to obtain the compound (I). Pramipexole, a compound with dopamine D-2 agonist activity, is among the compounds (I) and is useful for the treatment of Parkinson's disease and schizophrenia.Type: GrantFiled: November 16, 2009Date of Patent: January 25, 2011Assignee: Ragactives, S.L.Inventors: Gustavo Pascual Coca, Jorge Martin Juarez
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Patent number: 7842821Abstract: The invention is aimed at a compound of formula (I) wherein n is 0, 1 or 2, R1 is a linear or branched alkyl group, R2 is selected from a substituted or non substituted alkyl group, substituted or non substituted aryl group, substituted or non substituted aralkyl group, substituted or non substituted heterocyclyl group, or a substituted or non substituted heterocyclylalkyl group. Another object of the invention is a process for obtaining these compounds from the corresponding compound with a hydroxy group in position 4 by means of reacting with a sulfonamide in the presence of a phosphine and a dialkyl azadicarboxylate. The deprotection of the compound of formula (I) gives rise to the corresponding amine. The intermediate and the processes described are very useful in the synthesis of pharmaceutical products.Type: GrantFiled: November 4, 2005Date of Patent: November 30, 2010Assignee: Ragactives, S.L.Inventors: José María Gorgojo Lobato, Luis Octavio Silva Guisasola, Jorge Martín Juárez
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Patent number: 7795435Abstract: The process includes the steps of (i) dissolving finasteride in a substantially anhydrous organic solvent selected among n-butyl acetate, iso-butyl acetate, sec-butyl acetate, tert-butyl acetate, C5 alkyl acetate and mixtures thereof, at a temperature equal to or lower than the boiling point of said organic solvent; (ii) slowly cooling said finasteride solution to a cooling temperature determined on the basis of the chosen solvent; (iii) maintaining the resulting suspension at the cooling temperature for a period of time equal to or less than 16 hours; and (iv) recovering the resulting solid phase containing Form I of finasteride, for example by means of filtration, and removing the solvent, for example by means of drying said crystals. The process allows for obtaining the Form I of finasteride only and in a pure form.Type: GrantFiled: April 29, 2005Date of Patent: September 14, 2010Assignee: Ragactives, S.L.Inventors: Luis Octavio Silva Guisasola, Mario Laderas Muñoz, Jorge Martin Juarez
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Publication number: 20100063324Abstract: The present invention relates to a process for preparing 2-amino-6-alkyl-amino-4,5,6,7-tetrahydrobenzothiazoles (I) wherein the asterisk (*) represents an asymmetric carbon and R1 is C1-C6 alkyl; their enantiomers or mixtures thereof, their solvates, hydrates or pharmaceutically acceptable salts, comprising: (a) reacting a compound (II) with a secondary amine, optionally in the presence of an acid and a solvent 1, to form an enamine; (b) optionally removing said acid and said solvent 1, and then reacting said enamine with sulfur in the presence of a solvent 2; and (c) reacting the previously obtained compound with cyanamide to obtain the compound (I). Pramipexole, a compound with dopamine D-2 agonist activity, is among the compounds (I) and is useful for the treatment of Parkinson's disease and schizophrenia.Type: ApplicationFiled: November 16, 2009Publication date: March 11, 2010Applicant: RAGACTIVES, S.L.Inventors: Gustavo Pascual Coca, Jorge Martín Juárez
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Patent number: 7638542Abstract: A process for preparing 2-amino-6-alkyl-amino-4,5,6,7-tetrahydrobenzothiazoles of formula (I) wherein the asterisk (*) represents an asymmetric carbon and R1 is C1-C6 alkyl; and enantiomers and mixtures thereof, and their solvates, hydrates and pharmaceutically acceptable salts. The process involves (a) reacting with a secondary amine, optionally in the presence of an acid and a first solvent, to form an enamine; (b) optionally removing the acid and first solvent, and then reacting the enamine with sulfur in the presence of a second solvent; and (c) reacting the previously obtained compound with cyanamide to obtain the formula (I) compound. Pramipexole, a dopamine D-2 agonist, can be made by such process, and is useful for the treatment of Parkinson's disease and schizophrenia.Type: GrantFiled: June 24, 2005Date of Patent: December 29, 2009Assignee: Ragactives, S.L.Inventors: Gustavo Pascual Coca, Jorge Martín Juárez
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Publication number: 20090076287Abstract: The invention is aimed at a compound of formula (I) wherein n is 0, 1 or 2, R1 is a linear or branched alkyl group, R2 is selected from a substituted or non substituted alkyl group, substituted or non substituted aryl group, substituted or non substituted aralkyl group, substituted or non substituted heterocyclyl group, or a substituted or non substituted heterocyclylalkyl group. Another object of the invention is a process for obtaining these compounds from the corresponding compound with a hydroxy group in position 4 by means of reacting with a sulfonamide in the presence of a phosphine and a dialkyl azadicarboxylate. The deprotection of the compound of formula (I) gives rise to the corresponding amine. The intermediate and the processes described are very useful in the synthesis of pharmaceutical products.Type: ApplicationFiled: November 4, 2005Publication date: March 19, 2009Applicant: RAGACTIVES, S.L.Inventors: Jose Maria Gorgojo Lobato, Luis Octavio Silva Guisasola, Jorge Martin Juarez
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Patent number: 7473805Abstract: The process comprises reacting a compound of formula (II), where R is a hydroxyl protecting group, and the asterisk indicates an asymmetric carbon atom, with diisopropylamine in the presence of a reducing agent; optionally converting the resulting intermediate into a salt and, if so desired, isolating it; removing the hydroxyl protecting group; and if so desired, separating the desired (R) or (S) enantiomer, or the mixture of enantiomers and/or converting the obtained compound into a pharmaceutically acceptable salt thereof. Tolterodine is a muscarinic receptor antagonist useful in treating urinary incontinence and other symptoms of urinary bladder hyperactivity.Type: GrantFiled: December 21, 2004Date of Patent: January 6, 2009Assignee: Ragactives, S.L. Parque Tecnologico de BoecilloInventors: Gustavo Pascual Coca, Pablo Martin Pascual, Jorge Martin Juarez
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Publication number: 20080194832Abstract: The invention relates to a novel method for the resolution of the racemic mixture of compound (R,S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole, or the enrichment of same with in one of its enantiomers, and to intermediate compounds which can be used to perform said method.Type: ApplicationFiled: May 9, 2006Publication date: August 14, 2008Applicant: Ragactives, S.L.Inventors: Luis Octavio Silva Guisasola, Jorge Martin Juarez
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Publication number: 20070254959Abstract: The process comprises reacting a compound of formula (II), where R is a hydroxyl protecting group, and the asterisk indicates an asymmetric carbon atom, with diisopropylamine in the presence of a reducing agent; optionally converting the resulting intermediate into a salt and, if so desired, isolating it; removing the hydroxyl protecting group; and if so desired, separating the desired (R) or (S) enantiomer, or the mixture of enantiomers and/or converting the obtained compound into a pharmaceutically acceptable salt thereof. Tolterodine is a muscarinic receptor antagonist useful in treating urinary incontinence and other symptoms of urinary bladder hyperactivity.Type: ApplicationFiled: December 21, 2004Publication date: November 1, 2007Applicant: RAGACTIVES, S.L.Inventors: Gustavo Pascual Coca, Pablo Martin Pascual, Jorge Martin Juarez
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Patent number: 7105698Abstract: The process for separating the R(?)- and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-sulfonamide enantiomers comprises (a) reacting a mixture of said enantiomers with an optically active organic acid to form diastereoisomeric salts with said enantiomers, where in said diastereoisomeric salts have different solubility and can be separated by crystallization; (b) separating the diastereoisomeric salt mixture enriched in the salt of one of the enantiomers; and (c) releasing said salts to obtain the R(?)or S(+) enantiomer. The R(?)-5-[2-[[2-(2-ethoxyphenoxy) ethyl]amino]propyl]-2-methoxybenzenesulfonamide enantiomer has ?-adrenergic blocking activity and is useful as an antihypertensive agent suitable for the treatment of congestive heart failure and benign prostatic hypertrophy.Type: GrantFiled: March 12, 2004Date of Patent: September 12, 2006Assignee: Ragactives, S.L.Inventors: Cristina Blanco Fernandez, Antonio Lorente Bonde-Larsen, Jorge Martin Juarez, Luis Octavio Silva Guisasola
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Patent number: 7057045Abstract: The 17?-(substituted)-3-oxo-?1,2-4-azasteroids (I), wherein R1 is C1–C4 alkyl, OR2, wherein R2 is a C1–C4 alkyl radical, or NR3R4, wherein R3 and R4, equal or different, represent hydrogen or a C1–C4 alkyl radical, can be obtained by means of a process comprising cleaving the oxazolidinedione ring present in a 2-(substituted)-3-hydroxyoxazolidinedione of formula (IV), wherein R5 is Br or trichloromethylsulfonyl, and removing the substituent at position 2, to form a double bond at position 1,2. Some compounds (I) are testosterone-5?-reductase inhibitors and can be used in the treatment of hyperandrogenic disorders.Type: GrantFiled: March 26, 2004Date of Patent: June 6, 2006Assignee: Ragactives, S.L.Inventors: Jose Maria Gorgojo Lobato, Antonio Lorente Bonde-Larsen, Jorge Martin Juarez
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Publication number: 20040254209Abstract: The 17&bgr;-(substituted)-3-oxo-&Dgr;1,2-4-azasteroids (I), wherein R1 is C1-C4 alkyl, OR2, wherein R2 is a C1-C4 alkyl radical, or NR3R4, wherein R3 and R4, equal or different, represent hydrogen or a C1-C4 alkyl radical, can be obtained by means of a process comprising cleaving the oxazolidinedione ring present in a 2-(substituted)-3-hydroxyoxazolidinedione of formula (IV), wherein R5 is Br or trichloromethylsulfonyl, and removing the substituent at position 2, to form a double bond at position 1,2. Some compounds (I) are testosterone-5&agr;-reductase inhibitors and can be used in the treatment of hyperandrogenic disorders.Type: ApplicationFiled: March 26, 2004Publication date: December 16, 2004Applicant: Ragactives, S.L.Inventors: Jose Maria Gorgojo Lobato, Antonio Lorente Bonde-Larsen, Jorge Martin Juarez
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Publication number: 20040181055Abstract: 6&agr;-fluorpregnanes (I), where the dotted line between positions 1 and 2 represents a single or double bond; R1 is OH, OCOR2, X, SO3R3, or an (R7)(R8)(R9)SiO— group, where X is halogen, R2 and R3 are C1-6 alkyl or phenyl optionally substituted by C1-4 alkyl, and R7, R8 and R9, equal or different, are C1-6 alkyl or phenyl optionally substituted by C1-4 alkyl, can be obtained by means of a high stereoselectivity process comprising reacting a 3-(trisubstituted)silyloxy-pregna-3,5-diene (IV) with a fluorinating agent selected among N-fluorosulfonimides and N-fluorosulfonamides. The 6&agr;-fluorpregnanes (I) are intermediates for the synthesis of steroids useful as anti-inflammatory and anti-asthmatic agents.Type: ApplicationFiled: January 26, 2004Publication date: September 16, 2004Applicant: Ragactives, S.L.Inventors: Jose Vicente Murillo Garrido, Luis Octavio Silva Guisasola, Jorge Martin Juarez
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Publication number: 20030220509Abstract: The process for obtaining 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-2-sulfonamide-7,7-dioxides (I) wherein R1 is H or C1-5 alkyl, and R2 is C1-5 alkyl, starts from the corresponding 4-(N-alkylamino)-5,6-dihydro-4H-thien-(2,3-b)-thiopyran-7,7-dioxides, and comprises protecting the alkylamine group, introducing a sulfonamide group and eliminating protecting group. Some compounds of formula (I) are inhibitors of the carbonic anhydrase and can be used in the treatment of elevated intraocular pressure.Type: ApplicationFiled: March 3, 2003Publication date: November 27, 2003Applicant: RAGACTIVES, S.L.Inventors: Pablo Garcia Losada, Luis Octavio Silva Guisasola, Antonio Lorente Bonde-Larsen, Jorge Martin Juarez