KR101953270B1 - 무정형 레터모비어 및 그의 경구 투여용 고체 제약 제제 - Google Patents

무정형 레터모비어 및 그의 경구 투여용 고체 제약 제제 Download PDF

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KR101953270B1
KR101953270B1 KR1020167001010A KR20167001010A KR101953270B1 KR 101953270 B1 KR101953270 B1 KR 101953270B1 KR 1020167001010 A KR1020167001010 A KR 1020167001010A KR 20167001010 A KR20167001010 A KR 20167001010A KR 101953270 B1 KR101953270 B1 KR 101953270B1
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amorphous
minutes
dissolution
acetonitrile
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KR20160029075A (ko
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빌프리에트 슈바프
디르크 정
크리스티안 쉬카네더
벨자네 매르텐스
마카엘 리메르트
클레멘스 보테
마티아스 베르베
니콜 린데르만
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아이쿠리스 안티-인펙티브 큐어스 게엠베하
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C07D239/84—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1611—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Virology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
KR1020167001010A 2013-06-19 2014-06-19 무정형 레터모비어 및 그의 경구 투여용 고체 제약 제제 Active KR101953270B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP13003120 2013-06-19
EP13003120.6 2013-06-19
EP14165027 2014-04-16
EP14165027.5 2014-04-16
PCT/EP2014/062974 WO2014202737A1 (en) 2013-06-19 2014-06-19 Amorphous letermovir and solid pharmaceutical formulations thereof for oral administration

Publications (2)

Publication Number Publication Date
KR20160029075A KR20160029075A (ko) 2016-03-14
KR101953270B1 true KR101953270B1 (ko) 2019-02-28

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US (1) US10442773B2 (enExample)
EP (1) EP3010891B1 (enExample)
JP (2) JP6445546B2 (enExample)
KR (1) KR101953270B1 (enExample)
CN (2) CN105555771B (enExample)
AU (1) AU2014283231B2 (enExample)
BR (1) BR112015031979B1 (enExample)
CA (1) CA2916143C (enExample)
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CY (1) CY1121732T1 (enExample)
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DO (1) DOP2015000303A (enExample)
EA (1) EA036131B1 (enExample)
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IL (2) IL243228B (enExample)
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MD (1) MD4673C1 (enExample)
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PH (1) PH12015502821B1 (enExample)
PL (1) PL3010891T3 (enExample)
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RS (1) RS58882B1 (enExample)
SG (1) SG11201510426PA (enExample)
SI (1) SI3010891T1 (enExample)
SM (1) SMT201900327T1 (enExample)
UA (1) UA117755C2 (enExample)
WO (1) WO2014202737A1 (enExample)
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DE10319612A1 (de) * 2003-05-02 2004-11-18 Bayer Healthcare Ag Substituierte Dihydrochinazoline
DE102012101673A1 (de) 2012-02-29 2013-08-29 Aicuris Gmbh & Co. Kg Salze eines Dihydrochinazolinderivats
PL3010891T3 (pl) * 2013-06-19 2019-11-29 Aicuris Anti Infective Cures Gmbh Amorficzny letermowir i jego stałe preparaty farmaceutyczne do podawania doustnego
US11413295B2 (en) 2016-03-31 2022-08-16 Intercept Pharmaceuticals, Inc. Oral preparation of obeticholic acid
AU2020237505B2 (en) * 2019-03-12 2023-02-02 Microbiotix, Inc. Combination drug treatment for human cytomegalovirus
CN111024861A (zh) * 2019-12-31 2020-04-17 山东省药学科学院 一种莱特莫韦及含莱特莫韦的制剂中有关物质的检测方法
EP3906929A1 (en) 2020-05-08 2021-11-10 AiCuris GmbH & Co. KG Letermovir for use in the prevention and the treatment of coronavirus infections
US20230312485A1 (en) 2020-08-17 2023-10-05 Lupin Limited A precipitation process for amorphous letermovir
US20240041882A1 (en) * 2020-12-16 2024-02-08 Merck Sharp & Dohme Llc Mini-tablet dosage form of a viral terminase inhibitor and uses thereof
CN115403528B (zh) * 2021-05-27 2025-01-07 南京正大天晴制药有限公司 无定形3,4-二氢喹唑啉衍生物的制备方法
CN114942278B (zh) * 2022-04-12 2023-09-08 山东诚创蓝海医药科技有限公司 来特莫韦中间体二d-(+)-二对甲基苯甲酰酒石酸乙酸乙酯络合物有关物质的分析方法
WO2024037485A1 (zh) * 2022-08-15 2024-02-22 上海迪赛诺化学制药有限公司 一种来特莫韦无定形的制备方法
CN116338119A (zh) * 2023-02-24 2023-06-27 重庆希韦医药科技有限公司 一种来特莫韦包合物溶液体外释放度的测定方法
WO2025133248A1 (en) 2023-12-21 2025-06-26 Aic246 Ag & Co. Kg Diastereomeric aminoalcohol and aminoether salts of 2-[(4r,s)-8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl]acetic acid and their use for enantiomeric separation
JP2025161786A (ja) * 2024-04-12 2025-10-24 東和薬品株式会社 レテルモビル含有医薬組成物ならびにその製造方法および用途
CN119745803A (zh) * 2024-12-30 2025-04-04 上海奥科达医药科技股份有限公司 一种来特莫韦制剂组合物及其制备方法
CN120927867A (zh) * 2025-10-11 2025-11-11 成都诺和晟欣生物医药有限公司 一种来特莫韦注射液中对映异构体的hplc检测方法

Citations (2)

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US20070066622A1 (en) * 2003-02-12 2007-03-22 Tobias Wunberg 2-(3-Phenyl-2-piperazinyl-3,4-dihydroquinazolin-4-yl)acetic acids as antiviral agents, especially against cytomegaloviruses
US20090221822A1 (en) * 2005-06-15 2009-09-03 Bayer Healthcare Ag Process for the Preparation of Dihydroquinazolines

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DE10207026A1 (de) * 2002-02-20 2003-08-28 Boehringer Ingelheim Kg Pulverinhalativum, enthaltend den CGRP-Antagonisten BIBN4096 und Verfahren zu dessen Herstellung
DE10319612A1 (de) * 2003-05-02 2004-11-18 Bayer Healthcare Ag Substituierte Dihydrochinazoline
DE10338402A1 (de) * 2003-08-18 2005-03-17 Boehringer Ingelheim Pharma Gmbh & Co. Kg Sprühgetrocknetes, amorphes BIBN 4096, Verfahren zu dessen Herstellung sowie dessen Verwendung als Inhalativum
JP2008535924A (ja) * 2005-04-12 2008-09-04 エラン ファーマ インターナショナル リミテッド ナノ粒子キナゾリン誘導体製剤
KR20140022855A (ko) * 2011-05-04 2014-02-25 머크 샤프 앤드 돔 코포레이션 C형 간염 바이러스의 억제제의 제조 방법
DE102012101673A1 (de) * 2012-02-29 2013-08-29 Aicuris Gmbh & Co. Kg Salze eines Dihydrochinazolinderivats
DE102012101680A1 (de) * 2012-02-29 2013-08-29 Aicuris Gmbh & Co. Kg Pharmazeutische Zubereitung enthaltend ein antiviral wirksames Dihydrochinazolinderivat
DE102012101659A1 (de) * 2012-02-29 2013-08-29 Aicuris Gmbh & Co. Kg Salze eines Dihydrochinazolinderivats
WO2014047562A2 (en) * 2012-09-21 2014-03-27 Epiphany Biosciences Method of treating and/or preventing shingles and method of treating and/or preventing zoster associated pain
PL3010891T3 (pl) * 2013-06-19 2019-11-29 Aicuris Anti Infective Cures Gmbh Amorficzny letermowir i jego stałe preparaty farmaceutyczne do podawania doustnego

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070066622A1 (en) * 2003-02-12 2007-03-22 Tobias Wunberg 2-(3-Phenyl-2-piperazinyl-3,4-dihydroquinazolin-4-yl)acetic acids as antiviral agents, especially against cytomegaloviruses
US20090221822A1 (en) * 2005-06-15 2009-09-03 Bayer Healthcare Ag Process for the Preparation of Dihydroquinazolines

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MY179502A (en) 2020-11-09
BR112015031979B1 (pt) 2022-05-24
SI3010891T1 (sl) 2019-09-30
DOP2015000303A (es) 2016-01-15
AU2014283231A1 (en) 2016-01-21
JP2016522238A (ja) 2016-07-28
MD20150126A2 (ro) 2016-06-30
CU24619B1 (es) 2022-08-09
BR112015031979A2 (pt) 2017-07-25
CN105555771B (zh) 2025-02-21
EA201600024A1 (ru) 2016-12-30
IL263978B (en) 2020-07-30
HRP20190936T1 (hr) 2019-10-04
PE20160659A1 (es) 2016-07-24
IL243228B (en) 2020-04-30
JP2018193401A (ja) 2018-12-06
EP3010891B1 (en) 2019-04-10
JP6445546B2 (ja) 2018-12-26
IL263978A (en) 2019-01-31
ZA201509239B (en) 2022-03-30
CA2916143A1 (en) 2014-12-24
LT3010891T (lt) 2019-08-26
CN120097924A (zh) 2025-06-06
CA2916143C (en) 2019-01-29
UA117755C2 (uk) 2018-09-25
IL243228A0 (en) 2016-02-29
EP3010891A1 (en) 2016-04-27
NZ715387A (en) 2018-02-23
JP6770035B2 (ja) 2020-10-14
SMT201900327T1 (it) 2019-07-11
MX373764B (es) 2020-03-24
MD4673C1 (ro) 2020-11-30
HK1223935A1 (en) 2017-08-11
ES2730958T3 (es) 2019-11-13
PH12015502821B1 (en) 2019-09-25
RS58882B1 (sr) 2019-08-30
US10442773B2 (en) 2019-10-15
SG11201510426PA (en) 2016-01-28
BR112015031979A8 (pt) 2018-01-23
CY1121732T1 (el) 2020-07-31
WO2014202737A1 (en) 2014-12-24
MX2015017758A (es) 2016-06-21
HUE043721T2 (hu) 2019-09-30
EA036131B1 (ru) 2020-10-01
PL3010891T3 (pl) 2019-11-29
PT3010891T (pt) 2019-06-21
AU2014283231B2 (en) 2017-12-07
CU20150179A7 (es) 2016-07-29
CN105555771A (zh) 2016-05-04
US20160145216A1 (en) 2016-05-26
KR20160029075A (ko) 2016-03-14
MD4673B1 (ro) 2020-02-29
ME03483B (me) 2020-01-20
PH12015502821A1 (en) 2016-03-21
DK3010891T3 (da) 2019-06-24

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Patent event date: 20160114

Patent event code: PA01051R01D

Comment text: International Patent Application

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