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HK1208164A1 - Compositions comprising short-acting benzodiazepines - Google Patents

Compositions comprising short-acting benzodiazepines Download PDF

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Publication number
HK1208164A1
HK1208164A1 HK15108782.8A HK15108782A HK1208164A1 HK 1208164 A1 HK1208164 A1 HK 1208164A1 HK 15108782 A HK15108782 A HK 15108782A HK 1208164 A1 HK1208164 A1 HK 1208164A1
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HK
Hong Kong
Prior art keywords
composition
dextran
lactose
lyophilized
benzodiazepine
Prior art date
Application number
HK15108782.8A
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English (en)
French (fr)
Chinese (zh)
Other versions
HK1208164B (en
Inventor
John Aitken Graham
Alan James Baillie
Kevin Richard WARD
Thomas Peacock
Original Assignee
武汉人福创新药物研发中心有限公司
Priority date (The priority date 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 date listed.)
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=48669863&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HK1208164(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by 武汉人福创新药物研发中心有限公司 filed Critical 武汉人福创新药物研发中心有限公司
Publication of HK1208164A1 publication Critical patent/HK1208164A1/en
Publication of HK1208164B publication Critical patent/HK1208164B/en

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    • 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
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/55131,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/55171,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • 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
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/55131,4-Benzodiazepines, e.g. diazepam or clozapine
    • 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
    • A61K47/26Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02Muscle relaxants, e.g. for tetanus or cramps
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00Anaesthetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/141,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/161,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/141,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/161,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/181,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K47/36Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40Cyclodextrins; Derivatives thereof

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (12)

  1. Lyophilisierte oder sprühgetrocknete Zusammensetzung, umfassend wenigstens ein Benzodiazepin gemäß der Formel (I) wobei
    W H ist;
    X CH2 ist; n 1 ist;
    Y CH2 ist; m 1 ist;
    Z O ist;
    R1 CH3, CH2CH3, CH2CH2CH3, CH(CH3)2 oder CH2CH(CH3)2 ist;
    R2 2-Fluorphenyl, 2-Chlorphenyl oder 2-Pyridyl ist;
    R3 Cl oder Br ist;
    R4, R5 und R6 die Gruppe -CR8=U-V= bildet, wobei R8 Wasserstoff, C1-4-Alkyl oder C1-3-Hydroxyalkyl ist, U N oder CR9 ist, wobei R9 H, C1-4-Alkyl, C1-3-Hydroxyalkyl oder C1-4-Alkoxy ist, V N oder CH ist, und p Null ist;
    oder ein pharmazeutisch akzeptables Salz davon, wobei die Zusammensetzung
    wenigstens einen pharmazeutisch akzeptablen hygroskopischen Arzneiträger umfasst, wobei der hygroskopische Arzneiträger ein Kohlenhydrat ist, das ausgewählt ist aus der Gruppe bestehend aus Disacchariden und Dextran, und wobei die Zusammensetzung optional wenigstens teilweise amorph ist.
  2. Zusammensetzung nach Anspruch 1, wobei das Benzodiazepin gemäß Formel (I) Methyl 3-[(4S)-8-brom-1-methyl-6-(pyridin-2-yl)-4H-imidazol[1,2-a][1,4]benzodiazepin-4-yl]propanoat (Remimazolam) ist.
  3. Zusammensetzung nach Anspruch 2, wobei das pharmazeutisch akzeptable Salz des Benzodiazepins in kationischer Form formuliert ist, und wobei das Gegenion Benzolsulfonat (Besylat) ist.
  4. Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei das Dextran ein Molekulargewicht von 150 kD besitzt.
  5. Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei das Disaccharid ausgewählt ist aus der Gruppe bestehend aus Laktose, Maltose, Saccharose, und Trehalose.
  6. Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei die Zusammensetzung ein Gemisch aus einem ersten hygroskopischen Arzneiträger und einem zweiten hygroskopischen Arzneiträger umfasst.
  7. Zusammensetzung nach Anspruch 6, wobei die Zusammensetzung ein Gemisch aus Disaccharid und Dextran umfasst, vorzugsweise ein Gemisch aus Laktose und Dextran.
  8. Zusammensetzung nach Anspruch 7, wobei das Gewichtsverhältnis zwischen Laktose und Dextran zwischen 1:1,0 und 1:10 liegt, vorzugsweise zwischen 1:1,2 und 1:5 und darüber hinaus bevorzugt 1:1,5 oder 1:4.
  9. Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei das Gewichtsverhältnis zwischen der Gesamtmenge hygroskopischer Arzneiträger und der Gesamtmenge an Benzodiazepinen oder Salzen davon, berechnet für die Base, in der Zusammensetzung zwischen 20:1 und 1:1 liegt, vorzugsweise zwischen 12:1 und 3:1, wobei ein Wert zwischen 9:1 und 3:1 am meisten bevorzugt ist.
  10. Zusammensetzung nach einem der Ansprüche 1 bis 3, bei der es sich um eine pharmazeutische Formulierung handelt.
  11. Verwendung eines Gemischs aus wenigstens einem Disaccharid und wenigstens einem Dextran für die Herstellung einer lyophilisierten oder sprühgetrockneten pharmazeutischen Zusammensetzung, umfassend ein Benzodiazepin mit einem Carbonsäureesteranteil gemäß Anspruch 1 oder ein pharmazeutisch akzeptables Salz davon, insbesondere Remimazolam.
  12. Verfahren zur Herstellung einer pharmazeutischen Zusammensetzung, die folgenden Schritte umfassend:
    a) Bereitstellen einer Lösung, umfassend ein Benzodiazepin nach Anspruch 1 oder ein pharmazeutisch akzeptables Salz davon, insbesondere Remimazolam;
    b) Zugabe wenigstens eines hygroskopischen Arzneiträgers, bei dem es sich um ein Kohlenhydrat handelt, das ausgewählt ist aus der Gruppe bestehend aus Disacchariden und Dextran oder einem Gemisch davon mit wenigstens einem weiteren hygroskopischen Arzneiträger;
    c) Trocknen der Lösung aus Schritt b) durch Lyophilisation oder Sprühtrocknen.
HK15108782.8A 2012-05-22 2013-05-22 Compositions comprising short-acting benzodiazepines HK1208164B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12168968 2012-05-22
EP12168968.1 2012-05-22
PCT/EP2013/060543 WO2013174883A1 (en) 2012-05-22 2013-05-22 Compositions comprising short-acting benzodiazepines

Publications (2)

Publication Number Publication Date
HK1208164A1 true HK1208164A1 (en) 2016-02-26
HK1208164B HK1208164B (en) 2018-06-29

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Also Published As

Publication number Publication date
CA2874247C (en) 2020-07-28
IL235789B (en) 2019-07-31
PL2852389T4 (pl) 2022-02-21
LTC2852389I2 (de) 2024-11-25
SG11201407710VA (en) 2015-01-29
ES2651389T3 (es) 2018-01-26
GEAP201813666A (en) 2018-01-25
CN108578413A (zh) 2018-09-28
ZA201408412B (en) 2016-09-28
US20150148338A1 (en) 2015-05-28
CN104968348A (zh) 2015-10-07
MX2014014225A (es) 2015-06-17
JP2015517552A (ja) 2015-06-22
HUE037734T2 (hu) 2018-09-28
SI2852389T1 (en) 2018-02-28
AU2013265295A1 (en) 2015-01-22
AP2014008084A0 (en) 2014-11-30
AR092008A1 (es) 2015-03-18
EP2852389B1 (de) 2017-10-18
IL235789A0 (en) 2015-01-29
TW201400119A (zh) 2014-01-01
TN2014000479A1 (en) 2016-03-30
MX368854B (es) 2019-10-18
PH12014502608A1 (en) 2015-01-21
NL301130I1 (de) 2021-09-22
LUC00230I2 (de) 2022-10-07
NZ702063A (en) 2016-11-25
GEP20186852B (en) 2018-05-25
MA37581B1 (fr) 2016-07-29
CO7151503A2 (es) 2014-12-29
BR112014029108A2 (pt) 2017-06-27
EA201492160A1 (ru) 2015-10-30
FR21C1043I2 (fr) 2022-10-07
TWI590826B (zh) 2017-07-11
JP6313286B2 (ja) 2018-04-18
PT2852389T (pt) 2017-12-13
LT2852389T (lt) 2017-12-27
ECSP14032553A (es) 2018-11-30
LTPA2021521I1 (de) 2021-10-11
CA2874247A1 (en) 2013-11-28
EA032119B1 (ru) 2019-04-30
CN104968348B (zh) 2018-04-17
MY185117A (en) 2021-04-30
MA20150233A1 (fr) 2015-07-31
EP2852389A1 (de) 2015-04-01
US20220040198A1 (en) 2022-02-10
DK2852389T3 (en) 2017-12-18
HUS2100040I1 (hu) 2021-10-28
NO2021041I1 (no) 2021-09-20
KR20150009601A (ko) 2015-01-26
PE20150683A1 (es) 2015-06-03
KR102116737B1 (ko) 2020-05-29
HRP20171872T1 (hr) 2018-02-23
AU2013265295B2 (en) 2017-08-31
FR21C1043I1 (de) 2021-11-19
PL2852389T3 (pl) 2018-02-28
RS56660B1 (sr) 2018-03-30
PH12014502608B1 (en) 2019-11-27
NO2852389T3 (de) 2018-03-17
WO2013174883A1 (en) 2013-11-28
CL2014003171A1 (es) 2015-06-19
UA115063C2 (uk) 2017-09-11
BR112014029108B1 (pt) 2022-02-08
NL301130I2 (nl) 2021-10-25

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