Patents Assigned to CRYSTAL PHARMA, S.A.U.
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Patent number: 12227537Abstract: Compounds having the formula or solvates of the compounds can be used as intermediates in the preparation of the synthetic steroids, Etonogestrel and Desogestrel, as well as other pharmaceutically active agents.Type: GrantFiled: May 13, 2021Date of Patent: February 18, 2025Assignee: CRYSTAL PHARMA, S.A.U.Inventors: Celso Miguel Sandoval Rodríguez, Ignacio Herráiz Sierra, Ivano Messina, Jesús Miguel Iglesias Retuerto
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Patent number: 12209107Abstract: The invention relates to an efficient and industrially applicable process for the preparation and purification of allopregnanolone and intermediates thereof without the assistance of column chromatography.Type: GrantFiled: March 18, 2020Date of Patent: January 28, 2025Assignee: CRYSTAL PHARMA, S.A.U.Inventors: Ivano Messina, Jesús Miguel Iglesias Retuerto, Ana María Ares Sacristán
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Patent number: 11312708Abstract: A process for preparing compounds of formula (I), or a salt or solvate thereof, including Brexpiprazole, which process comprises cyclization of a compound of formula (II) or (III), or a salt or solvate thereof. The invention also refers to intermediates of said process.Type: GrantFiled: February 7, 2020Date of Patent: April 26, 2022Assignee: CRYSTAL PHARMA, S.A.U.Inventors: Alfonso Pérez Encabo, José Ángel Turiel Hernandez, Yolanda Fernández Sainz, Antonio Lorente Bonde-Larsen
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Patent number: 11104702Abstract: A process for the preparation of obeticholic acid and derivatives thereof by: (a) hydrogenation of the double bond and reductive opening of the epoxide of a compound of formula (II) or a salt or solvate thereof to obtain a compound of formula (IIIa) and/or (IIIb), or salts or solvates thereof and (b) conversion of a compound of formula (IIIa) and/or a compound of formula (IIIb), or a salt or solvate thereof, into a compound of formula (I), or a salt or solvate thereofType: GrantFiled: June 22, 2018Date of Patent: August 31, 2021Assignee: CRYSTAL PHARMA, S.A.U.Inventors: Ignacio Herráiz Sierra, Yolanda Fernández Sainz, Carlos Cordovilla Losada, Alfonso Pérez Encabo, José Angel Turiel Hernandez
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Patent number: 11034716Abstract: A process for the preparation of 11-methylene steroids from di-keto steroids involves selective olefination of the ketone at position 11 of the di-keto steroids. The resulting 11-methylene steroid products can be used as intermediates in the preparation of the synthetic steroids, Etonogestrel and Desogestrel, as well as other pharmaceutically active agents.Type: GrantFiled: March 2, 2017Date of Patent: June 15, 2021Assignee: CRYSTAL PHARMA, S.A.U.Inventors: Celso Miguel Sandoval Rodríguez, Ignacio Herráiz Sierra, Ivano Messina, Jesús Miguel Iglesias Retuerto
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Patent number: 10597386Abstract: A process for preparing compounds of formula (I), or a salt or solvate thereof, including Brexpiprazole, which process comprises cyclization of a compound of formula (II) or (III), or a salt or solvate thereof. The invention also refers to intermediates of said process.Type: GrantFiled: September 30, 2016Date of Patent: March 24, 2020Assignee: Crystal Pharma, S.A.U.Inventors: Alfonso Pérez Encabo, José Ángel Turiel Hernandez, Yolanda Fernández Sainz, Antonio Lorente Bonde-Larsen
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Patent number: 10040765Abstract: The invention relates to new and improved processes for the preparation of Indacaterol and pharmaceutically acceptable salts thereof as well as intermediates for the preparation of Indacaterol. The new process avoids the use of the epoxide compound known in the art and the impurities associated therewith and results in a higher yield.Type: GrantFiled: September 28, 2016Date of Patent: August 7, 2018Assignee: Crystal Pharma S.A.U.Inventors: Antonio Lorente Bonde-Larsen, Yolanda Fernández Sainz, Jesús Iglesias Retuerto, Javier Gallo Nieto
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Patent number: 9988417Abstract: The invention relates to a process for obtaining Estetrol or a salt or solvate thereof, the process comprising: a) reacting a compound of formula (IV) or a salt or solvate thereof, wherein R1 is a hydroxyl protecting group selected from a silyl ether, an ether, an ester, a carbamate and a carbonate, and R2 is a hydroxyl protecting group selected from an ether, with an oxidizing agent selected from OsO4 or a source of osmium tetroxide to produce Estetrol or a compound of formula (II) or a salt or solvate thereof wherein R1 is as defined previously; and b) if a compound of formula (II) is obtained in step a), deprotecting said compound to produce Estetrol.Type: GrantFiled: September 17, 2014Date of Patent: June 5, 2018Assignee: Crystal Pharma, S.A.U.Inventors: Juan José Ferreiro Gil, Jesús Miguel Iglesias Retuerto, Francisco Javier Gallo Nieto
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Patent number: 9682984Abstract: The invention relates to new and improved processes for the preparation of Alcaftadine and pharmaceutically acceptable salts thereof as well as an intermediate for the preparation of Alcaftadine. The new process saves a number of steps compared to the known process and results in a higher yield.Type: GrantFiled: March 24, 2014Date of Patent: June 20, 2017Assignee: Crystal Pharma S.A.U.Inventors: Antonio Lorente Bonde-Larsen, Jesús Miguel Iglesias Retuerto, Franciso Javiér Gallo Nieto, Juan José Ferreiro Gil
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Patent number: 9475772Abstract: The invention relates to new and improved processes for the preparation of Indacaterol and pharmaceutically acceptable salts thereof as well as intermediates for the preparation of Indacaterol. The new process avoids the use of the epoxide compound known in the art and the impurities associated therewith and results in a higher yield.Type: GrantFiled: September 9, 2013Date of Patent: October 25, 2016Assignee: Crystal Pharma S.A.U.Inventors: Antonio Lorente Bonde-Larsen, Yolanda Fernández Sainz, Jesús Iglesias Retuerto, Javier Gallo Nieto
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Patent number: 9422228Abstract: 3,3-diphenylpropylamines of general formula (I), particularly Fesoterodine, as well as their enantiomers, solvates and salts, can be produced by treating a compound of formula (II) with a chiral alcohol to yield the diastereomeric esters of formula (IV) and (IV?), which can be further transformed into a compound of formula (I), or an enantiomer, solvate or salt thereof, wherein R1 is C1-C8 alkyl; and R2 and R3, independently of one another, represent H or C1-C6 alkyl, or together form a ring of 3 to 7 members with the nitrogen to which they are bound.Type: GrantFiled: April 26, 2013Date of Patent: August 23, 2016Assignee: CRYSTAL PHARMA, S.A.U.Inventors: Antonio Lorente Bonde-Larsen, Francisco Javier Gallo Nieto, Juan José Ferreiro Gil, Pablo Martín Pascual
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Publication number: 20160229885Abstract: The invention relates to a process for obtaining Estetrol or a salt or solvate thereof, the process comprising: a) reacting a compound of formula (IV) or a salt or solvate thereof, wherein R1 is a hydroxyl protecting group selected from a silyl ether, an ether, an ester, a carbamate and a carbonate, and R2 is a hydroxyl protecting group selected from an ether, with an oxidizing agent selected from OsO4 or a source of osmium tetroxide to produce Estetrol or a compound of formula (II) or a salt or solvate thereof wherein R1 is as defined previously; and b) if a compound of formula (II) is obtained in step a), deprotecting said compound to produce Estetrol.Type: ApplicationFiled: September 17, 2014Publication date: August 11, 2016Applicant: CRYSTAL PHARMA, S.A.U.Inventors: Juan José FERREIRO GIL, Jesús Miguel IGLESIAS RETUERTO, Francisco Javier GALLO NIETO
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Patent number: 9296780Abstract: A process ethynylates 16-methylene-17-keto steroids to the corresponding 16-methylene-17?-ethynyl-17?-hydroxy steroids by treatment with silyl-protected lithium acetylides followed by further desilylation. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as e.g. Nestorone® or melengestrol acetate.Type: GrantFiled: December 19, 2012Date of Patent: March 29, 2016Assignees: Crystal Pharma, S.A.U., Population Council Inc.Inventors: Luis Gerardo Gutiérrez Fuentes, Celso Miguel Sandoval Rodriguez
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Patent number: 9000195Abstract: 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: GrantFiled: July 14, 2009Date of Patent: April 7, 2015Assignee: Crystal Pharma, S.A.U.Inventors: Luis Octavio Silva Guisasola, Lydia Mateos Burón, Antonio Lorente Bonde-Larsen, Luis Gerardo Gutiérrez Fuentes
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Patent number: 8952173Abstract: 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: GrantFiled: May 9, 2006Date of Patent: February 10, 2015Assignee: Crystal Pharma, S.A.U.Inventors: Luis Octavio Silva Guisasola, Jorge Martin Juarez
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Publication number: 20150005518Abstract: A process ethynylates 16-methylene-17-keto steroids to the corresponding 16-methylene-17?-ethynyl-17?-hydroxy steroids by treatment with silyl-protected lithium acetylides followed by further desilylation. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as e.g. Nestorone® or melengestrol acetate.Type: ApplicationFiled: December 19, 2012Publication date: January 1, 2015Applicants: CRYSTAL PHARMA, S.A.U., THE POPULATION COUNCIL INC.Inventors: Luis Gerardo Gutiérrez Fuentes, Celso Miguel Sandoval Rodríguez
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Patent number: 8765785Abstract: The invention concerns fumarate salts of solifenacin, as well as pharmaceutical compositions comprising fumarate salts of solifenacin. The invention furthermore concerns a process for preparing solifenacin and salts thereof. The fumarate salt provides improved properties over the known solifenacin salts, especially in terms of its stability. The novel process for its preparation is furthermore improved over known processes for preparing solifenacin in that it provides a higher yield and recovers a greater amount of starting material.Type: GrantFiled: July 5, 2011Date of Patent: July 1, 2014Assignee: Crystal Pharma, S.A.U.Inventors: Gerardo Gutiérrez Fuentes, Antonio Lorente Bonde-Larsen, Jaime del Campo López-Bachiller, Celso Sandoval Rodríguez, Yolanda Fernández Sainz
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Patent number: 8722920Abstract: The invention relates to a process for obtaining 3,3-diphenylpropylamines of general formula (I), particularly Fesoterodine, as well as their enantiomers, solvates and salts, comprising a chemoselective reduction of the acid group against the ester group in compounds of general formula (V), wherein R1 is C1-C8 alkyl; and R3 and R4, independently of one another, represent H or C1-C8 alkyl, or together form a ring of 3 to 7 members with the nitrogen to which they are bound. The invention also relates to the compounds of formula (V), as well as their enantiomers, solvates and salts.Type: GrantFiled: July 26, 2010Date of Patent: May 13, 2014Assignee: Crystal Pharma S.A.U.Inventors: Antonio Lorente Bonde-Larsen, Pablo Martín Pascual, Mario Laderas Muñoz, Luis Gerardo Gutiérrez Fuentes
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Publication number: 20140011992Abstract: The present invention relates to processes for obtaining abiraterone and derivatives thereof, such as abiraterone acetate, by means of a Suzuki coupling through a steroid borate of general formula (IV) or a C—C coupling through a steroid hydrazone of general formula (II), as well as to intermediates useful in said processes.Type: ApplicationFiled: December 20, 2012Publication date: January 9, 2014Applicant: CRYSTAL PHARMA, S.A.U.Inventors: Alfonso Perez Encabo, Jose Angel Turiel Hernandez, Francisco Javier Gallo Nieto, Antonio Lorente Bonde-Larsen, Celso Miguel Sandoval Rodriguez
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Publication number: 20130203804Abstract: The invention concerns fumarate salts of solifenacin, as well as pharmaceutical compositions comprising fumarate salts of solifenacin. The invention furthermore concerns a process for preparing solifenacin and salts thereof. The fumarate salt provides improved properties over the known solifenacin salts, especially in terms of its stability. The novel process for its preparation is furthermore improved over known processes for preparing solifenacin in that it provides a higher yield and recovers a greater amount of starting material.Type: ApplicationFiled: July 5, 2011Publication date: August 8, 2013Applicant: CRYSTAL PHARMA, S.A.U.Inventors: Gerardo Gutiérrez Fuentes, Antonio Lorente Bonde-Larsen, Jaime del Campo López-Bachiller, Celso Sandoval Rodríguez, Yolanda Fernández Sainz