CA2916143C - Amorphous letermovir and solid pharmaceutical formulations thereof for oral administration - Google Patents

Amorphous letermovir and solid pharmaceutical formulations thereof for oral administration Download PDF

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Publication number
CA2916143C
CA2916143C CA2916143A CA2916143A CA2916143C CA 2916143 C CA2916143 C CA 2916143C CA 2916143 A CA2916143 A CA 2916143A CA 2916143 A CA2916143 A CA 2916143A CA 2916143 C CA2916143 C CA 2916143C
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CA
Canada
Prior art keywords
letermovir
amorphous
solid pharmaceutical
dissolution
minutes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2916143A
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English (en)
French (fr)
Other versions
CA2916143A1 (en
Inventor
Wilfried Schwab
Dirk Jung
Christian Schickaneder
Welljanne Martens
Michael Limmert
Clemens Bothe
Mathias Berwe
Nicole RINDERMANN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AIC246 AG and Co KG
Original Assignee
Aicuris Anti Infectives Cures GmbH
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Publication of CA2916143A1 publication Critical patent/CA2916143A1/en
Application granted granted Critical
Publication of CA2916143C publication Critical patent/CA2916143C/en
Active legal-status Critical Current
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/78Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C07D239/84Nitrogen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38Cellulose; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/20Antivirals for DNA viruses

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
  • Physiology (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)
CA2916143A 2013-06-19 2014-06-19 Amorphous letermovir and solid pharmaceutical formulations thereof for oral administration Active CA2916143C (en)

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
CA2916143A1 CA2916143A1 (en) 2014-12-24
CA2916143C true CA2916143C (en) 2019-01-29

Family

ID=50982905

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2916143A Active CA2916143C (en) 2013-06-19 2014-06-19 Amorphous letermovir and solid pharmaceutical formulations thereof for oral administration

Country Status (34)

Country Link
US (1) US10442773B2 (cg-RX-API-DMAC7.html)
EP (1) EP3010891B1 (cg-RX-API-DMAC7.html)
JP (2) JP6445546B2 (cg-RX-API-DMAC7.html)
KR (1) KR101953270B1 (cg-RX-API-DMAC7.html)
CN (2) CN105555771B (cg-RX-API-DMAC7.html)
AU (1) AU2014283231B2 (cg-RX-API-DMAC7.html)
BR (1) BR112015031979B1 (cg-RX-API-DMAC7.html)
CA (1) CA2916143C (cg-RX-API-DMAC7.html)
CU (1) CU24619B1 (cg-RX-API-DMAC7.html)
CY (1) CY1121732T1 (cg-RX-API-DMAC7.html)
DK (1) DK3010891T3 (cg-RX-API-DMAC7.html)
DO (1) DOP2015000303A (cg-RX-API-DMAC7.html)
EA (1) EA036131B1 (cg-RX-API-DMAC7.html)
ES (1) ES2730958T3 (cg-RX-API-DMAC7.html)
HR (1) HRP20190936T1 (cg-RX-API-DMAC7.html)
HU (1) HUE043721T2 (cg-RX-API-DMAC7.html)
IL (2) IL243228B (cg-RX-API-DMAC7.html)
LT (1) LT3010891T (cg-RX-API-DMAC7.html)
MD (1) MD4673C1 (cg-RX-API-DMAC7.html)
ME (1) ME03483B (cg-RX-API-DMAC7.html)
MX (1) MX373764B (cg-RX-API-DMAC7.html)
MY (1) MY179502A (cg-RX-API-DMAC7.html)
NZ (1) NZ715387A (cg-RX-API-DMAC7.html)
PE (1) PE20160659A1 (cg-RX-API-DMAC7.html)
PH (1) PH12015502821B1 (cg-RX-API-DMAC7.html)
PL (1) PL3010891T3 (cg-RX-API-DMAC7.html)
PT (1) PT3010891T (cg-RX-API-DMAC7.html)
RS (1) RS58882B1 (cg-RX-API-DMAC7.html)
SG (1) SG11201510426PA (cg-RX-API-DMAC7.html)
SI (1) SI3010891T1 (cg-RX-API-DMAC7.html)
SM (1) SMT201900327T1 (cg-RX-API-DMAC7.html)
UA (1) UA117755C2 (cg-RX-API-DMAC7.html)
WO (1) WO2014202737A1 (cg-RX-API-DMAC7.html)
ZA (1) ZA201509239B (cg-RX-API-DMAC7.html)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
KR101953270B1 (ko) * 2013-06-19 2019-02-28 아이쿠리스 안티-인펙티브 큐어스 게엠베하 무정형 레터모비어 및 그의 경구 투여용 고체 제약 제제
CA3019508A1 (en) 2016-03-31 2017-10-05 Intercept Pharmaceuticals, Inc. Oral preparation having exceptional elutability
US20220152028A1 (en) * 2019-03-12 2022-05-19 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
WO2022038457A1 (en) 2020-08-17 2022-02-24 Lupin Limited A precipitation process for amorphous letermovir
WO2022132676A1 (en) * 2020-12-16 2022-06-23 Merck Sharp & Dohme Corp. 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
TW202535393A (zh) 2023-12-21 2025-09-16 德商Aic246股份兩合公司 2-[(4r,s)-8-氟-2-[4-(3-甲氧基苯基)哌嗪-1-基]-3-[2-甲氧基-5-(三氟甲基)苯基]-3,4-二氫喹唑啉-4-基]乙酸之非鏡像異構物胺基醇鹽及胺基醚鹽及其於鏡像異構物分離之用途
WO2025216283A1 (ja) * 2024-04-12 2025-10-16 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

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
DE10305785A1 (de) * 2003-02-12 2004-08-26 Bayer Healthcare Ag 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
CN101198314A (zh) * 2005-04-12 2008-06-11 伊兰制药国际有限公司 纳米微粒喹唑啉衍生物制剂
DE102005027517A1 (de) * 2005-06-15 2006-12-21 Bayer Healthcare Ag Verfahren zur Herstellung von Dihydrochinazolinen
WO2012151271A1 (en) * 2011-05-04 2012-11-08 Merck Sharp & Dohme Corp. Processes for preparing inhibitors of the hepatitis c virus
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
KR101953270B1 (ko) * 2013-06-19 2019-02-28 아이쿠리스 안티-인펙티브 큐어스 게엠베하 무정형 레터모비어 및 그의 경구 투여용 고체 제약 제제

Also Published As

Publication number Publication date
SMT201900327T1 (it) 2019-07-11
EA036131B1 (ru) 2020-10-01
KR101953270B1 (ko) 2019-02-28
US20160145216A1 (en) 2016-05-26
HUE043721T2 (hu) 2019-09-30
MX2015017758A (es) 2016-06-21
ZA201509239B (en) 2022-03-30
SI3010891T1 (sl) 2019-09-30
ES2730958T3 (es) 2019-11-13
UA117755C2 (uk) 2018-09-25
MD4673B1 (ro) 2020-02-29
IL263978A (en) 2019-01-31
CA2916143A1 (en) 2014-12-24
BR112015031979B1 (pt) 2022-05-24
EP3010891B1 (en) 2019-04-10
PT3010891T (pt) 2019-06-21
DK3010891T3 (da) 2019-06-24
DOP2015000303A (es) 2016-01-15
PE20160659A1 (es) 2016-07-24
LT3010891T (lt) 2019-08-26
RS58882B1 (sr) 2019-08-30
MD20150126A2 (ro) 2016-06-30
JP6770035B2 (ja) 2020-10-14
BR112015031979A2 (pt) 2017-07-25
CN105555771A (zh) 2016-05-04
ME03483B (me) 2020-01-20
PH12015502821A1 (en) 2016-03-21
MX373764B (es) 2020-03-24
EP3010891A1 (en) 2016-04-27
WO2014202737A1 (en) 2014-12-24
HRP20190936T1 (hr) 2019-10-04
JP2016522238A (ja) 2016-07-28
MY179502A (en) 2020-11-09
BR112015031979A8 (pt) 2018-01-23
CU24619B1 (es) 2022-08-09
IL243228B (en) 2020-04-30
JP6445546B2 (ja) 2018-12-26
JP2018193401A (ja) 2018-12-06
PL3010891T3 (pl) 2019-11-29
KR20160029075A (ko) 2016-03-14
PH12015502821B1 (en) 2019-09-25
MD4673C1 (ro) 2020-11-30
CU20150179A7 (es) 2016-07-29
CN105555771B (zh) 2025-02-21
AU2014283231B2 (en) 2017-12-07
NZ715387A (en) 2018-02-23
CY1121732T1 (el) 2020-07-31
SG11201510426PA (en) 2016-01-28
AU2014283231A1 (en) 2016-01-21
HK1223935A1 (en) 2017-08-11
CN120097924A (zh) 2025-06-06
US10442773B2 (en) 2019-10-15
EA201600024A1 (ru) 2016-12-30
IL263978B (en) 2020-07-30
IL243228A0 (en) 2016-02-29

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