Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-215/56
A61K-031/47
출원번호
US-0272692
(2014-05-08)
등록번호
US-9139530
(2015-09-22)
발명자
/ 주소
Hurter, Patricia
Rowe, William
Young, Christopher R.
Costache, Adriana
Connelly, Patrick R.
Krawiec, Mariusz
Gong, Yuchuan
Feng, Yushi
Trudeau, Martin
출원인 / 주소
Vertex Pharmaceuticals Incorporated
대리인 / 주소
Honigman Miller Schwartz and Cohn LLP
인용정보
피인용 횟수 :
27인용 특허 :
72
초록
The present invention relates to solid state forms of N-2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl-1,4-dihydro-4-oxoquinoline-3-carboxamide (Compound 1), pharmaceutical compositions thereof and methods therewith.
대표청구항▼
1. A crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide, characterized as Form A, wherein the Form A is characterized by one or more peaks at 5.0 and 15.6 degrees in an X-ray powder diffraction pattern obtained using Cu K alpha radiation. 2. Form
1. A crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide, characterized as Form A, wherein the Form A is characterized by one or more peaks at 5.0 and 15.6 degrees in an X-ray powder diffraction pattern obtained using Cu K alpha radiation. 2. Form A of claim 1, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 7.8. 3. Form A of claim 2, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 8.5. 4. Form A of claim 3, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 9.2. 5. Form A of claim 4, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 9.9. 6. Form A of claim 5, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 11.9. 7. Form A of claim 6, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 12.6. 8. Form A of claim 7, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 13.9. 9. Form A of claim 8, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 14.9. 10. Form A of claim 9, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 16.5. 11. Form A of claim 10, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 18.1. 12. Form A of claim 11, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 18.5. 13. Form A of claim 12, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 20.7. 14. Form A of claim 13, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 22.0. 15. Form A of claim 14, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 23.5. 16. Form A of claim 15, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 25.3. 17. Form A of claim 16, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 28.0. 18. Form A of claim 17, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 29.4. 19. Form A of claim 18, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak 30.9. 20. A pharmaceutical composition comprising the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide according to claim 1, and a pharmaceutically acceptable adjuvant or carrier. 21. A process for preparing Form A of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide according to claim 1, wherein said process comprises the step of heating N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide to about 250° C. and cooling to room temperature. 22. A method for treating a disease in a mammal comprising administering Form A of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide according to claim 1, wherein said disease is selected from cystic fibrosis, hereditary emphysema, COPD, and dry-eye disease. 23. The method of claim 22, wherein the Form A of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is in a pharmaceutical composition. 24. The method according to claim 22, wherein the method comprises administering an additional therapeutic agent. 25. A pharmaceutical pack or kit comprising Form A of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide according to claim 1 and a pharmaceutically acceptable carrier. 26. The method according to claim 22, wherein said disease is cystic fibrosis. 27. Form A of claim 1, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peaks: 9.9, 14.9, 18.1, and 28.0. 28. Form A of claim 27, wherein the crystal form of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide is further characterized by the following peak: 30.9.
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Sofia Michael J. (Carmel IN), 1,2,4-trioxygenated benzene derivatives useful as leukotriene antagonists.
Witzel Bruce E. (Westfield NJ) Tolman Richard L. (Warren NJ) Rasmusson Gary H. (Watchung NJ) Bakshi Raman K. (Edison NJ) Yang Shu Shu (Bridgewater NJ), 17-Ethers and thioethers of 4-aza-steroids.
Clemence Fran ois (Paris FRX) Le Martret Odile (Paris FRX) Delevallee Fran oise (Fontenay-sous-Bois FRX), 4-OH-quinoline carboxylic acid amides having analgesic and anti-inflammatory activity.
Mendes Etienne (Toulouse FRX) Vernieres Jean-Claude (Muret FRX) Keane Peter E. (Garonne FRX) Bachy Andr (Toulouse FRX), 4-amino quinolines and naphthyridines and their use as medicines.
Afonso Adriano (West Caldwell NJ) Weinstein Jay (Upper Montclair NJ) Gentles Margaret J. (Bloomfield NJ) Rosenblum Stuart B. (West Orange NJ), Acyl and alkoxy substituted quinolines.
Strobel,Hartmut; Wohlfart,Paulus; Safarova,Alena; Walser,Armin; Suzuki,Teri; Sch?nafinger,Karl, Acylated indanyl amines and their use as pharmaceuticals.
Ryder Hamish,GBX ; Ashworth Philip Anthony,GBX ; Roe Michael Bryan,GBX ; Brumwell Julie Elizabeth,GBX ; Hunjan Sukhjit,GBX ; Folkes Adrian John,GBX ; Sanderson Jason Terry,GBX ; Williams Susannah,GBX, Anthranilic acid derivatives as multi drug resistance modulators.
Culbertson Townley P. (Ann Arbor MI) Domagala John M. (Canton MI) Mich Thomas F. (Ann Arbor MI) Nichols Jeffrey B. (Ypsilanti MI), Antibacterial agents.
Afonso Adriano (West Caldwell NJ) Weinstein Jay (Upper Montclair NJ) Gentles Margaret J. (Bloomfield NJ), Antiviral compounds and antihypertensive compounds.
Sabatucci, Joseph P.; Caufield, Craig E.; Greenfield, Alexander A.; Morris, Koi M.; Morrison, Eamonn P., Aryl substituted 3-ethoxy phenyl trifluoromethane sulfonamides for the treatment of non-insulin dependent diabetes mellitus (NIDDM).
Marfat Anthony (Mystic CT) Eggler James F. (Stonington CT) Fray Michael J. (Wingham CT GBX) Cooper Kelvin (Noank CT), Azabenzimidazoles in the treatment of asthma, arthritis and related diseases.
Blum Charles A. ; DeSimone Robert ; Hutchison Alan ; Peterson John M., Certain amido- and amino- substituted benzylamine derivatives; a new class of neuropeptide Y1 specific ligands.
Dumaitre Bernard Andre (Les Ulis FRX) Dodic Nerina (Les Ulis FRX) Daugan Alain Claude-Marie (Les Ulis FRX) Pianetti Pascal Maurice Charles (Les Ulis FRX), Certain isoquinoline derivatives having anti-tumor properties.
Young, Christopher R.; Rowe, Charles William, Compositions of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1, 4-dihydro-4-oxoquinoline-3-carboxamide.
Witzel Bruce E. (Westfield NJ) Rasmusson Gary H. (Watchung NJ) Tolman Richard L. (Warren NJ) Yang Shu Shu (Bridgewater NJ), Ester derivatives of 4-aza-steroids.
Batchelor Mark James,GBX ; Bebbington David,GBX ; Bemis Guy W. ; Fridman Wolf Herman,FRX ; Gillespie Roger John,GBX ; Golec Julian M. C.,GBX ; Lauffer David J. ; Livingston David J. ; Matharu Saroop , Inhibitors of interleukin-1.beta. converting enzyme.
Bradford C. Van Wagenen ; Scott T. Moe ; Daryl L. Smith ; Susan M. Sheehan ; Irina Shcherbakova ; Richard Travato ; Ruth Walton ; Robert Barmore ; Eric G. Delmar ; Thomas M. Stormann, Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases.
Baudry Alain (Gonesse FRX) Junino Alex (Livry-Gargan FRX) Richard Herv (Paris FRX), Method for dyeing keratinous fibres using an aminoindole in combination with a quinone derivative.
Kerwin, Sean M.; Hurley, Laurence H.; DeLuca, Mark R.; Moore, III, Bob M.; Mundy, Gregory R., Methods and compositions for stimulating osteoblast proliferation or treating malignant cell proliferation and methods for selecting osteoblast proliferation stimulants.
Clemence Francois (Paris FRX) Hunt Peter F. (Gonesse FRX) Le Martret Odile (Paris FRX) Humbert Daniel (Fontenay Sous Bois FRX), N-(4,5-Dihydro-thiazol-2-yl)-3-quinoline-carboxamides having anxiolytic activity.
Charvet-Faury Anne Sophie,FRX ; Camplo Michel,FRX ; Kraus Jean Louis,FRX, N4-substituted cytosinyl 1,3-oxathiolane nucleoside analogues, and their antiviral activity.
Bunker, Amy Mae; Harter, William Glen; Hicks, James Lester; O'Brien, Patrick Michael; Pham, Ly; Picard, Joseph Armand; Roark, William Howard, Phenylene alkyne matrix metalloproteinase inhibitors.
Grohe Klaus (Odenthal DEX) Zeiler Hans-Joachim (Velbert DEX) Metzger Karl G. (Wuppertal DEX), Process for the preparation of 4-pyridone-3-carboxylic acids and/or derivatives thereof.
Strehlke, Peter; Droescher, Peter; Buehmann, Ulrich; Schmees, Norbert; Muhn, Peter; Hess-Stumpp, Holger; Kühne, Roland; Guenther, Eckhard; Polymeropoulos, Emmanuel; Ter Laak, Antonius M., Quinoline, isoquinoline and phthalazine derivatives as antagonists of the gonadotropin-releasing hormone.
Schriewer Michael (Odenthal DEX) Grohe Klaus (Odenthal DEX) Petersen Uwe (Leverkusen DEX), Quinolone- and 1,8-naphthyridin-4-one-carboxylic acids which are C-bonded in the 7-position.
Beasley Steven Colin,GBX ; Montana John Gary,GBX ; Dyke Hazel Joan,GBX ; Haughan Alan Findlay,GBX ; Buckley George Martin,GBX ; Baxter Andrew Douglas,GBX, Quinolones and their therapeutic use.
Beasley Steven Colin,GBX ; Montana John Gary,GBX ; Dyke Hazel John,GBX ; Haughan Alan Findlay,GBX ; Runcie Karen Ann,GBX ; Manallack David Thomas,GBX ; Buckley George Martin,GBX ; Maxey Robert James,, Quinolones and their therapeutic use.
Lang Gerard (Saint-Gratien FRX) Junino Alex (Livry-Gargan FRX) Cotteret Jean (Verneuil-sur-Seine FRX) Vandenbossche Jean J. (Aulnay-sous-Bois FRX), Tinctorial composition for keratinous fibres containing oxidation dye precursors and aminoindole couplers, methods for d.
Hadida Ruah, Sara S.; Grootenhuis, Peter D. J.; Van Goor, Fredrick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel; Yang, Xiaoqing, Modulators of ATP-binding cassette transporters.
Hadida Ruah, Sara S.; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel, Modulators of ATP-binding cassette transporters.
Hadida Ruah, Sara Sabina; Grootenhuis, Peter Diederik Jan; Van Goor, Fredrick F.; Zhou, Jinglan; Bear, Brian Richard; Miller, Mark Thomas; McCartney, Jason; Numa, Mehdi Michel Djamel, Modulators of ATP-binding cassette transporters.
Hadida Ruah, Sara Sabina; Grootenhuis, Peter Diederik Jan; Van Goor, Fredrick F.; Zhou, Jinglan; Bear, Brian Richard; Miller, Mark Thomas; McCartney, Jason; Numa, Mehdi Michel Djamel, Modulators of ATP-binding cassette transporters.
DeMattei, John; Looker, Adam R.; Neubert-Langille, Bobbianna; Trudeau, Martin; Roeper, Stefanie; Ryan, Michael P.; Guerette, Dahrika Milfred Yap; Krueger, Brian R.; Grootenhuis, Peter D. J.; Van Goor, Fredrick F.; Botfield, Martyn C.; Zlokarnik, Gregor, Process for making modulators of cystic fibrosis transmembrane conductance regulator.
Demattei, John; Looker, Adam R.; Neubert-Langille, Bobbianna; Trudeau, Martin; Roeper, Stefanie; Ryan, Michael P.; Guerette, Dahrika Milfred Yap; Krueger, Brian R.; Grootenhuis, Peter D. J.; Van Goor, Fredrick F.; Botfield, Martyn C.; Zlokarnik, Gregor, Process for making modulators of cystic fibrosis transmembrane conductance regulator.
Swinney, Kelly Ann; Hurter, Patricia Nell; Nadig, David E.; Smith, David; Thomas, Vance Hayden; Warman, Martin Paul, Process of preparing pharmaceutical compositions for the treatment of CFTR mediated diseases.
Tanoury, Gerald J.; Harrison, Cristian; Littler, Benjamin Joseph; Rose, Peter Jamison; Hughes, Robert Michael; Jung, Young Chun; Siesel, David Andrew; Lee, Elaine Chungmin; Belmont, Daniel T.; Nugent, William A., Process of producing cycloalkylcarboxamido-indole compounds.
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