Title:
MEDICAL DRUG
Document Type and Number:
WIPO Patent Application WO/2018/159701
Kind Code:
A1
Abstract:
The present invention establishes a technology for stably formulating an isoquinoline-6-amino derivative as an ophthalmic agent or the like. Provided is a medicinal preparation that is produced by housing, in a polyolefin-based resin container, an aqueous composition containing a compound represented by general formula (1) (in the formula: R1 and R2 each independently represent a hydrogen atom or a C1-C4 alkyl group; R3 represents a hydrogen atom or a hydroxyl group; "A" denotes- CH(R4)- or -CH2-CH(R4)- (here, R4 is an optionally substituted C6-C10 aryl group or an optionally substituted 5 to 10-membered heteroaryl group); and formula (1) also includes a tautomer thereof) or a salt thereof, or a solvate thereof.
Inventors:
YAMAKITA YOSHIHIRO (JP)
Application Number:
PCT/JP2018/007582
Publication Date:
September 07, 2018
Filing Date:
February 28, 2018
Export Citation:
Assignee:
KOWA CO (JP)
International Classes:
A61K31/472; A61J1/05; A61K9/08; A61K31/4725; A61K47/04; A61K47/10; A61P27/02; A61P27/06; B65D1/00; B65D65/20
Domestic Patent References:
| WO2016047720A1 | 2016-03-31 | |||
| WO2005087237A1 | 2005-09-22 | |||
| WO2009091898A2 | 2009-07-23 |
Foreign References:
| JP2016515520A | 2016-05-30 | |||
| JP2016138085A | 2016-08-04 | |||
| JP2012525386A | 2012-10-22 | |||
| JP2016515520A | 2016-05-30 | |||
| JP2006249055A | 2006-09-21 | |||
| JP5477996B2 | 2014-04-23 | |||
| EP3199161B1 | 2021-12-15 |
Other References:
ELLIS, EYDIE MILLER ET AL.: "Ocular hypotensive effect of the novel EP 3/FP agonist ON0-9054 versus Xalatan: results of a 28-day, double-masked, randomised study", BRITISH JOURNAL OF OPHTHALMOLOGY, vol. 101, 20 September 2016 (2016-09-20), pages 796 - 800, XP055538363, ISSN: 1468-2079
LEVY, BRIAN ET AL.: "Ocular hypotensive safety and systemic absorption of AR -13324 ophthalmic solution in normal volunteers", AMERICAN JOURNAL OF OPHTHALMOLOGY, vol. 159, no. 5, May 2015 (2015-05-01), pages 980 - 985, XP055554459, ISSN: 0002-9394
REN, RUIYI ET AL.: "Netarsudil increases outflow facility in human eyes through multiple mechanisms", INVESTIGATIVE OPHTHALMOLOGY AND VISUAL SCIENCE, vol. 57, no. 14, November 2016 (2016-11-01), pages 6197 - 6209, XP055538365, ISSN: 1552-5783
"FOOD AND DRUG ADMINISTRATIONCenter for Drug Evaluation and ResearchOffice of Prescription Drug Promotion", RHOPRESSA™ (NETARSUDIL OPHTHALMIC SOLUTION) LABEL , NDA 208254 , REFERENCE ID:4194833, 15 November 2017 (2017-11-15), pages 4 - 10, XP055554465, Retrieved from the Internet
BACHARACH J. ET AL., OPHTHALMOLOGY, vol. 122, no. 2, 2015, pages 302 - 7
STURDIVANT JM. ET AL., BIOORG MED CHEM LETT., vol. 26, no. 10, 2016, pages 2475 - 80
WILLIAMS RD. ET AL., AM. J. OPHTHALMOL., vol. 152, no. 5, 2011, pages 834 - 41
JAMES SWARBRICK: "Encyclopedia of Pharmaceutical Technology, Third Edition", 1 January 2007, article MICHAEL J. AKERS: "Drug Delivery: Parenteral Route", pages: 1266 - 1278, XP055649126
"661 Containers-Plastics", THE UNITED STATES PHARMACOPEIA THE NATIONAL FORMULARY, vol. 1, no. USP 35 / NF 30, 1 May 2012 (2012-05-01), Rockville, Md., USA , pages 275 - 280, XP055862019, ISSN: 0195-7996
FDA: "LUMIGAN® 0.01% and 0.03% (bimatoprost ophthalmic solution)", HIGHLIGHTS OF PRESCRIBING INFORMATION, 1 March 2012 (2012-03-01), pages 3 - 10, XP055862024
DEAN ET AL.: "Pharmaceutical Packaging Technology", 2000, pages: 459pp
"Q1B Photostability Testing of New Drug Substances and Products", GUIDANCE FOR INDUSTRY, 1 November 1996 (1996-11-01), pages 1 - 11, XP055175855
EUROPEAN MEDICINES AGENCY (EMEA): "Note for Guidance on the Photostability Testing of New Active Substances and Medicinal Products", CPMP/ICH/279/95, 1 January 1998 (1998-01-01), pages 1 - 9, XP055459430
TONNESEN, H.H.: "Formulation and stability testing of photolabile drugs", INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 225, no. 1-2, 28 August 2001 (2001-08-28), NL , pages 1 - 14, XP027379967, ISSN: 0378-5173
OHASHI Y.: "Ganka New Insight", 10 July 1997, article AWATA, TAKASHI: "Chapter II - Developing Eye Drop Medicines", pages: 15 - 25, XP055862164
SINGH SHIVA P., STENBERG VIRGIL I., PARMAR SURENDRA S.: "Photochemistry of alkaloids", CHEMICAL REVIEWS, vol. 80, no. 3, 1 June 1980 (1980-06-01), US , pages 269 - 282, XP055862167, ISSN: 0009-2665, DOI: 10.1021/cr60325a004
CASTELLANO A., J.P. CATTEAU, A. LABLACHE-COMBIER: "Mechanism of the photochemical substitution of 6-membered ring monoazaaromatic compounds by methanolin neurtral and HCI acidified medium", TETRAHEDRON, vol. 31, no. 18, 1 January 1975 (1975-01-01), pages 2255 - 2261, XP055862181
STECK EDGAR A, EWING GALEN W: "Absorption Spectra of Heterocyclic Compounds. II. Amino-Derivatives of Pyridine, Quinoline and Isoquinoline", ABSORPTION SPECTRA OF PYRIDINES, QUINOLINES AND ISOQUINOLINES, vol. 70, no. 10, 1 October 1948 (1948-10-01), pages 3397 - 3406, XP055862186
HILBORN J W, MACKNIGHT E, PINCOCK J A, WEDGE P J: "Photochemistry of Substituted Benzyl Acetates and Benzyl Pivalates: A Reinvestigation of Substituent Effects", J. AM. CHEM. SOC., vol. 116, no. 8, 1 January 1994 (1994-01-01), pages 3337 - 3346, XP055862188
PINCOCK JAMES A.: "Photochemistry of Arylmethyl Esters in Nucleophilic Solvents: Radical Pair and Ion Pair Intermediates", ACCOUNTS OF CHEMICAL RESEARCH, ACS, vol. 30, no. 1, 1 January 1997 (1997-01-01), US , pages 43 - 49, XP055862191, ISSN: 0001-4842, DOI: 10.1021/ar960177r
FDA: "XALATAN® (latanoprost ophthalmic solution) 0.005%", HIGHLIGHTS OF PRESCRIBING INFORMATION, 1 June 2014 (2014-06-01), pages 4 - 13, XP055862196
ZHU DAZHANG, WANG SHILONG, SUN XIAOYU, NI YAMING, YAO SIDE: "Reaction mechanism studies on isoquinoline with hydroxyl radical in aqueous solutions", FRONTIERS OF CHEMISTRY IN CHINA, vol. 2, no. 4, 1 October 2007 (2007-10-01), pages 354 - 358, XP055979428, ISSN: 1673-3495, DOI: 10.1007/s11458-007-0067-8
WU YI ., SHUAI YIN HUA DENG BIAN: "Pharmaceutical preparations biopharmaceutical production technology Books(Chinese Edition)", 1 June 2015, GUANGDONG HIGHER EDUCATION PRESS. , article "Pharmaceutical preparations biopharmaceutical production technology Books(Chinese Edition) /Passage/", pages: 93 - 97, XP055979450
ZHAO CHUNJIE: "Pharmaceutical Professional Knowledge 1", 1 January 2015, PEOPLE’S ARMY MEDICAL PRESS, article "Pharmaceutical Professional Knowledge 1 /Passage/", pages: 48 - 57, XP055979457
JAN F. RABEK: "Polymer Photodegradation Mechanisms and Experimental Methods", 1 January 1995, SPRINGER SCIENCE+ BUSINESS MEDIA, DORDRECHT, article "Photodegradation and photo-oxidative degradation ", pages: 3pp, 70, 84, XP055979466
See also references of EP 3590513A4
LEVY, BRIAN ET AL.: "Ocular hypotensive safety and systemic absorption of AR -13324 ophthalmic solution in normal volunteers", AMERICAN JOURNAL OF OPHTHALMOLOGY, vol. 159, no. 5, May 2015 (2015-05-01), pages 980 - 985, XP055554459, ISSN: 0002-9394
REN, RUIYI ET AL.: "Netarsudil increases outflow facility in human eyes through multiple mechanisms", INVESTIGATIVE OPHTHALMOLOGY AND VISUAL SCIENCE, vol. 57, no. 14, November 2016 (2016-11-01), pages 6197 - 6209, XP055538365, ISSN: 1552-5783
"FOOD AND DRUG ADMINISTRATIONCenter for Drug Evaluation and ResearchOffice of Prescription Drug Promotion", RHOPRESSA™ (NETARSUDIL OPHTHALMIC SOLUTION) LABEL , NDA 208254 , REFERENCE ID:4194833, 15 November 2017 (2017-11-15), pages 4 - 10, XP055554465, Retrieved from the Internet
BACHARACH J. ET AL., OPHTHALMOLOGY, vol. 122, no. 2, 2015, pages 302 - 7
STURDIVANT JM. ET AL., BIOORG MED CHEM LETT., vol. 26, no. 10, 2016, pages 2475 - 80
WILLIAMS RD. ET AL., AM. J. OPHTHALMOL., vol. 152, no. 5, 2011, pages 834 - 41
JAMES SWARBRICK: "Encyclopedia of Pharmaceutical Technology, Third Edition", 1 January 2007, article MICHAEL J. AKERS: "Drug Delivery: Parenteral Route", pages: 1266 - 1278, XP055649126
"661 Containers-Plastics", THE UNITED STATES PHARMACOPEIA THE NATIONAL FORMULARY, vol. 1, no. USP 35 / NF 30, 1 May 2012 (2012-05-01), Rockville, Md., USA , pages 275 - 280, XP055862019, ISSN: 0195-7996
FDA: "LUMIGAN® 0.01% and 0.03% (bimatoprost ophthalmic solution)", HIGHLIGHTS OF PRESCRIBING INFORMATION, 1 March 2012 (2012-03-01), pages 3 - 10, XP055862024
DEAN ET AL.: "Pharmaceutical Packaging Technology", 2000, pages: 459pp
"Q1B Photostability Testing of New Drug Substances and Products", GUIDANCE FOR INDUSTRY, 1 November 1996 (1996-11-01), pages 1 - 11, XP055175855
EUROPEAN MEDICINES AGENCY (EMEA): "Note for Guidance on the Photostability Testing of New Active Substances and Medicinal Products", CPMP/ICH/279/95, 1 January 1998 (1998-01-01), pages 1 - 9, XP055459430
TONNESEN, H.H.: "Formulation and stability testing of photolabile drugs", INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 225, no. 1-2, 28 August 2001 (2001-08-28), NL , pages 1 - 14, XP027379967, ISSN: 0378-5173
OHASHI Y.: "Ganka New Insight", 10 July 1997, article AWATA, TAKASHI: "Chapter II - Developing Eye Drop Medicines", pages: 15 - 25, XP055862164
SINGH SHIVA P., STENBERG VIRGIL I., PARMAR SURENDRA S.: "Photochemistry of alkaloids", CHEMICAL REVIEWS, vol. 80, no. 3, 1 June 1980 (1980-06-01), US , pages 269 - 282, XP055862167, ISSN: 0009-2665, DOI: 10.1021/cr60325a004
CASTELLANO A., J.P. CATTEAU, A. LABLACHE-COMBIER: "Mechanism of the photochemical substitution of 6-membered ring monoazaaromatic compounds by methanolin neurtral and HCI acidified medium", TETRAHEDRON, vol. 31, no. 18, 1 January 1975 (1975-01-01), pages 2255 - 2261, XP055862181
STECK EDGAR A, EWING GALEN W: "Absorption Spectra of Heterocyclic Compounds. II. Amino-Derivatives of Pyridine, Quinoline and Isoquinoline", ABSORPTION SPECTRA OF PYRIDINES, QUINOLINES AND ISOQUINOLINES, vol. 70, no. 10, 1 October 1948 (1948-10-01), pages 3397 - 3406, XP055862186
HILBORN J W, MACKNIGHT E, PINCOCK J A, WEDGE P J: "Photochemistry of Substituted Benzyl Acetates and Benzyl Pivalates: A Reinvestigation of Substituent Effects", J. AM. CHEM. SOC., vol. 116, no. 8, 1 January 1994 (1994-01-01), pages 3337 - 3346, XP055862188
PINCOCK JAMES A.: "Photochemistry of Arylmethyl Esters in Nucleophilic Solvents: Radical Pair and Ion Pair Intermediates", ACCOUNTS OF CHEMICAL RESEARCH, ACS, vol. 30, no. 1, 1 January 1997 (1997-01-01), US , pages 43 - 49, XP055862191, ISSN: 0001-4842, DOI: 10.1021/ar960177r
FDA: "XALATAN® (latanoprost ophthalmic solution) 0.005%", HIGHLIGHTS OF PRESCRIBING INFORMATION, 1 June 2014 (2014-06-01), pages 4 - 13, XP055862196
ZHU DAZHANG, WANG SHILONG, SUN XIAOYU, NI YAMING, YAO SIDE: "Reaction mechanism studies on isoquinoline with hydroxyl radical in aqueous solutions", FRONTIERS OF CHEMISTRY IN CHINA, vol. 2, no. 4, 1 October 2007 (2007-10-01), pages 354 - 358, XP055979428, ISSN: 1673-3495, DOI: 10.1007/s11458-007-0067-8
WU YI ., SHUAI YIN HUA DENG BIAN: "Pharmaceutical preparations biopharmaceutical production technology Books(Chinese Edition)", 1 June 2015, GUANGDONG HIGHER EDUCATION PRESS. , article "Pharmaceutical preparations biopharmaceutical production technology Books(Chinese Edition) /Passage/", pages: 93 - 97, XP055979450
ZHAO CHUNJIE: "Pharmaceutical Professional Knowledge 1", 1 January 2015, PEOPLE’S ARMY MEDICAL PRESS, article "Pharmaceutical Professional Knowledge 1 /Passage/", pages: 48 - 57, XP055979457
JAN F. RABEK: "Polymer Photodegradation Mechanisms and Experimental Methods", 1 January 1995, SPRINGER SCIENCE+ BUSINESS MEDIA, DORDRECHT, article "Photodegradation and photo-oxidative degradation ", pages: 3pp, 70, 84, XP055979466
See also references of EP 3590513A4
Attorney, Agent or Firm:
THE PATENT CORPORATE BODY ARUGA PATENT OFFICE (JP)
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