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GB2558191A - Pharmaceutical composition - Google Patents

Pharmaceutical composition Download PDF

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Publication number
GB2558191A
GB2558191A GB1615917.0A GB201615917A GB2558191A GB 2558191 A GB2558191 A GB 2558191A GB 201615917 A GB201615917 A GB 201615917A GB 2558191 A GB2558191 A GB 2558191A
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Prior art keywords
weight
pharmaceutical composition
composition
acceptable salt
pharmaceutically acceptable
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GB201615917D0 (en
Inventor
Corr Stuart
James Noakes Timothy
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Mexichem Fluor SA de CV
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Mexichem Fluor SA de CV
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Priority to GB1615917.0A priority Critical patent/GB2558191A/en
Publication of GB201615917D0 publication Critical patent/GB201615917D0/en
Priority to UAA201902770A priority patent/UA123919C2/en
Priority to JP2019515227A priority patent/JP6781829B2/en
Priority to PCT/GB2017/052761 priority patent/WO2018051130A1/en
Priority to PE2019000674A priority patent/PE20191043A1/en
Priority to MYPI2019001316A priority patent/MY202069A/en
Priority to US16/334,158 priority patent/US10888546B2/en
Priority to ES19199780T priority patent/ES2968212T3/en
Priority to GEAP201715035A priority patent/GEP20217239B/en
Priority to ES17777635T priority patent/ES2892673T3/en
Priority to ES21183659T priority patent/ES2957459T3/en
Priority to MX2021009476A priority patent/MX392213B/en
Priority to EP17777635.8A priority patent/EP3515432B1/en
Priority to CN202210401223.3A priority patent/CN114712338A/en
Priority to EP21183659.8A priority patent/EP3915555B1/en
Priority to AU2017328907A priority patent/AU2017328907B2/en
Priority to CN201780057068.5A priority patent/CN109789126B/en
Priority to ES19199783T priority patent/ES2968453T3/en
Priority to EP19199780.8A priority patent/EP3607936B1/en
Priority to MX2019003098A priority patent/MX387723B/en
Priority to KR1020217021521A priority patent/KR20210089273A/en
Priority to NZ752430A priority patent/NZ752430B2/en
Priority to PH1/2019/500579A priority patent/PH12019500579B1/en
Priority to EP19199783.2A priority patent/EP3610871B1/en
Priority to CN202210090188.8A priority patent/CN114272238A/en
Priority to BR112019005133-3A priority patent/BR112019005133B1/en
Priority to CN202210090190.5A priority patent/CN114515284A/en
Priority to KR1020197010385A priority patent/KR102277635B1/en
Priority to CA3037092A priority patent/CA3037092C/en
Publication of GB2558191A publication Critical patent/GB2558191A/en
Priority to IL265360A priority patent/IL265360B2/en
Priority to MX2021009475A priority patent/MX2021009475A/en
Priority to SA519401336A priority patent/SA519401336B1/en
Priority to CONC2019/0002556A priority patent/CO2019002556A2/en
Priority to ZA2019/02053A priority patent/ZA201902053B/en
Priority to US16/582,993 priority patent/US11179366B2/en
Priority to US16/582,973 priority patent/US11103480B2/en
Priority to JP2020040655A priority patent/JP7041703B2/en
Priority to AU2020202626A priority patent/AU2020202626B2/en
Priority to US17/361,851 priority patent/US11826349B2/en
Priority to US17/361,819 priority patent/US11826348B2/en
Priority to US17/361,772 priority patent/US11642330B2/en
Priority to AU2021205045A priority patent/AU2021205045C1/en
Priority to US17/467,778 priority patent/US11690823B2/en
Priority to JP2022022292A priority patent/JP7228726B2/en
Priority to US18/489,150 priority patent/US20240050405A1/en
Priority to US18/489,133 priority patent/US20240050404A1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4704—2-Quinolinones, e.g. carbostyril
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • 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
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • 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
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/12—Mucolytics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Organic Chemistry (AREA)
  • Otolaryngology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A pharmaceutical composition suitable for use with a metered dose inhaler (MDI) comprises; (i) a drug component comprising at least one pharmaceutically acceptable salt of glycopyrrolate; and (ii) a propellant component comprising 1,1-difluoroethane (HFA-152a). Preferably, the glycopyrrolate is present as the bromide salt. Preferably, the composition further comprises at least one long acting beta-2-agoinst (LABA) (e.g. indacaterol, olodaterol, formoterol, vilanterol). Preferably, the composition additionally comprises at least one corticosteroid (e.g. budesonide, mometasone, beclomethasone, fluticasone). Preferably, the composition additionally comprises at least one surfactant compound (e.g. polyvinylpyrrolidone (PVP), polyethylene glycol (PEG), oleic acid, lecithin). Preferably, the composition contains less than 5 ppm water. In preferred embodiments the propellant is entirely HFA-152a. The composition may contain ethanol as a polar excipient. Also claimed is a method of improving the stability of a pharmaceutical composition comprising propellant and glycopyrrolate through use of HFA-152a as propellant.

Description

I, Copley Scientific, Nottingham UK) was connected to a vacuum pump (GE Motors, NJ, USA). Prior to testing, the cups of the NGI system were coated with 1 % v/v silicone oil in hexane to eliminate particle bounce. For each experiment, three actuations of the valve were discharged into the NGI at 30 L.mlrr as per pharmacopeia guidelines. Following aerosolization, the NGI apparatus was dismantled and the actuator and each part of the NGI was washed down Into known volumes of the HPLC mobile phase. The mass of drug deposited on each part of the NGI was determined by HPLC. This protocol was repeated three times for each canister, following which, the fine partible dose (FPD) and ffoe particle fraction of the emitted dose (FPFsn) were determined.
High performance liquid chromatography (HPLC) was used to determine drug content following aerosolteafipn studies (see below). A 250 mm x 4,6mm Hypersii ODS Ci» column with a 5 pm particle size (Fisher, Loughborough) or an equivalent was used for the analysis of fluticasone propionate, A 50 mm x 4.6 mm Necieosii 100 - 3 C«s HD column with a & pm particle size or ah equivalent was used for the analysis of glycopyrrohium bromide and indacatarol.
The columns were coupled to a UV detector operating at a wavelength of either 220 nm or235 nm depending on which drug was being analysed. The autosarapier was operated at ambient temperature and 100 pi samples were injected Info the column for the analyses:. The ehromatographlc conditions are shown in Tables 1 and 2 below.
Drug Pump Flow Rat© (mimin'1) Mobile Phase UV Wavelength (nm) Column Temperature (°C)
Fluticasone Propionate 1,5 Methanol, acetonitrile and water - 45:35:20 v/v 235 40
Table 2 Flow Rate Mobile Phase (mtmin !) J UV Wavelength (nm) Column Temperature (°C)
Glycopyrronium Bromide and Indacaterol I Mobile Phase A: Buffer* and i acetonitrile I 75:25 v/v I Mobile Phase i B: Buffer* and I acetonitrile I 25:75 v/v 220 30
* Buffer is aqueous Iriethylamine/NajHPQ.vH^PO/i at pH 2.5 26
The composition of the mobile phase: was varied as shown in Table 3 below,
Tabla 3
Time (minutes) i Mobile Phase A (%v/v) Mobile Phase B (%v/v)
0 | 100 0
3.0 I 85 15
3.1 0 100
4.0 ho 100
4.1 10Q 0
S.O Ε°° 0
The results are shown in Tables 4 to 8 below.
Table 4. fe wire aerosoilzation performance of combination formulations of giyoopyrronium bromide, indacaterol and fluticasone propionate delivered from a MD1 with HFA-134a as the propellant at time t “ 0 and after storage (valve down) for
1 month at 4QaC and 75 % relative humidity as characterised by the emitted dose, fine particle dose, fine particle fraction of the emitted dose (FPFeq {%)}, mass median aerodynamic diameter (MMAD) and geometric standard deviation (GSD).
Emitted Dose (pg + S.D.) Pine Particle Doss (ug .+ S.D.) FFFeq (%) MMAD + GBD (pm)
Glycopyrronium: Bromide (T ~ 0) 43 7 ± 0 2 12.6 + 0.1 28.7 + 0.2 2.6 + 2.4
Giyoopyrronium Bromide (Τ' ~ 1 month @ 4O’C/75% RH) 38.7 + 0.6 11.4 + 0.4 29.4 + 0.5 2.8 + 2.3
Indacaterol (T ~ 0 ) 75,8 + 1.8 23.8 + 0.8 31.5 ± 1.8 4.8+1,9
Indacaterol (T ~ 1 month @ 40*0/75% RH> 73.7+1.2 21.9 + 0.7 29.8 + 0.7 4.8 + 1.9
Fluticasone Propionate (T ~ 0) 116.0*2.0 38.8 + 1.7 32.8*0.9 3.0 * 1.8
Fluticasone Propionate (T --1 month 40*0/75% _RH)_ 112.8 ±2.3 32.8 * 1.9 29.0* 1.9 3.1 * 1.9
Table 5. fo v/tr© aerosoiixation performance of combination formulations of giycopyrroniurn bromide, indacaterol and fluticasone propionate delivered from a MDI with HFA-152a as the propellant at time t ~ 0 and after storage (valve down) for 1 month at 40°C and 75 % relative humidity as characterised by the emitted dose, '5 fine particle dose, fine particle fraction of the emitted dose (FPFh» (%)), mass median aerodynamic diameter (MMAD) and geometric standard deviation (GSB).
Emitted Dose (ug±S.D.) Frne Pan ce Dose (pg ± S D,) FPFe:· (%) MMAD ± GSD (pm)
Glycopyrronium Bromide (T ~ δ) 45.2 ±0.7 21.0 + 1.0 48.5 + 2,9 3,1 + 2.2
Glycopyrronium Bromide (T ::: 1 month @ 4CfC/75% RH) 44.2 ±0.8 20.7 ± 0.8 45.8 ± 1.8 3.0 ±2.2
Indacaterol (T ~ 0) 92.1 + 3.0 46.8 + 1.5 50.9 + 0.1 3.4 + 1,9
indacaterol (7 - 1 month @ 4O‘:C/75% RH) 00.8 ±2.3 45.8 + 1.2 49.5 * 0.2 3.5 *2.0
Fluticasone Propionate (T ~ 0) 111.8 ±0.7 51.5+1.9 46.1 ± 1.5 3.0 + 1,9
Fluticasone Propionate (7 - 1 month @ 4O’C/75% RH) 105.6 ±0.8 48.5 + 1.5 45.2 + 1.2 2.9 + 1.9
Table 6. Ratio of glycopyrronium bromide, indacaterol and fluticasone prooionafe in the delivered fine particle fraction using HFA-134a propellant ano HFA-152a propellant at time t “ 0 and after storage (valve down) for 1 month at 40°G and 75 % relative humidity,
Ratio of Glycopyrronium Bromide; indacateroi: Fi uticasone propionate
As formulated 1.0:2.0:2,5
HFA-134a - T = 0 1.0:1.9:3.1
HFA-T34a -7-1 month (£§ 10::C/75% RH) 1.0:1.9:2.9
HFA- 152a -7 = 0 1.0:2.2:2.5
HFA-134S-T- 1 month @ 40Έ/75% RH) 1.0:2,2:2.3
it Is dear from the data in Tables 4 and S above that the fine particle dose and the fine particle fraction of the emitted dose are sig nif lea π fly higher when HFA~l52a is used as the: propellant as opposed to HFA-134a for all three drugs in the combination drug formulation. This represents an Increase in the useful medication delivery dose. This improved performance is also observed even after stress storage for 1 month at 40'C and 75 % relative humidity
In contrast to the HrA-134a formulations: where ail of the drugs achieve a fine particle fraction of around: 39%, the HFA~i52 a formulations deliver a fine particle fraction of 45% to 50%, Thus, HFA-152a provides a dramatically more effective and efficient delivery of all three drugs with the significant benefits of reducing the amount of medication used to: deliver an effective therapeutic dose, reducing the cost of treatment and reducing the potential for systemic absorption: of the drugs: through the mouth and digestive tract resulting in adverse effects in the patient,
Furthermore., whilst the MMAD of the HFA-134a based formulations range from around 2.6um for giycopyrronlum bromide to 4.8pm for indadaterdi, the particles delivered by HFA-152a have broadly equivalent sizes in the range of from 2,9pm: to 3,5pm. This greater uniformity of particle size across the three drugs is extremely important In ensuring that all three drugs are delivered in the correct ratios to target lung tissue. Disparities in particle size can lead to non-uniform delivery with differential drug deposition and with consequential reduced therapeutic synergy between the drugs. Thus, the data Indicates that HFA-152a acts to minimise the extent of parti ole aggregation both for a particular drug and:
between the different drugs.
Examples
The stabilities of giycopyrronlum bromide, indacaferoi and fluticasone propionate in RFA-134 a and HFA-152a were investigated at time zero (T~0) and after storage, valve down, for 1 month (T~1 M) and 3 months (T~3M) at 4G°C and 75% relative humidity (RH) and: at 26°G and 60% relative humidity (RH) in uncoated aluminium cans
The drug formulations were prepared as described in Example 1 above and analysed using the HPLC technique described In Example 1 above.
The results of investigating: the chemical stability of the giyoopyrronlum bromide, indasateFoi and fluticasone propionate drug fonnuiafions in ;HFA~152a and HFAi 34a in uncoated aluminium cans are shown, respectively, in Tables 7 to 12 below:.
Table 7. Chemical stability of glycopyrronium bromide in HFA»134a in bncoated aluminium cans based on percentage assay and total impurities upon storage at T~0,
T~1M @ 4£HC/75 % RH and 25’C/80 % RH and T=3M@ 40fiC/75 % RH and 259C/60 % RH.
Time % Assay (LC) % total Impurities
Initial time F ~ 0 98.5 0.19
T ~ 1M @ 25/60 98.2 0.28
T 1M @40/75 97.8 0.39
T = 3M @ 25/60 94.8 1.15
T « 3M: @40/75 93.8 1.38
Table 8, Chemical stability of giycopynonium bromide in HFA-1S2a in uncoated aluminium cans based on percentage assay and total Impurities upon storage at T~0. T=1M @ 40°C/75 % RH and 25’C/SG % RH and T~3IV5@ 40°G/75 % RH and 2§*G/©S % RH
i ime % Assay (LC) % total impurities
Initial time T ~ 0 98.5 0.19
T = 1M @ 25/60 98.6 0.25
T = 1M @40/75 98.4 0.35
T - 3M @ 25/60 97.6 0.55
T = 3M @40/75 97.2 0.82
Table 9, Chemical stability of Indacaterol in HFA-134a in uncoated aluminium cans based on percentage assay and total impurities upon storage at T~0s T~1 M @ 40::C/75 % RH and 25βΟ/δδ % RH and T~3J¥i@ 4(RC/?5 % RH and 2.5=0/60 % RH.
Timo % Assay ί LG) % total impurities
Initial time T ~ © TOO.5 <LoQ
T~ 1M© 25/60 99.9 <LcQ
T = 1M ©40/75 96.0 0.22
T = 3M © 25/60 98.2 0.27
T = 3fvl ©40/75 97.9 0,38
Table 10. Chemical stability of indacaterol in HFA-152a in uncoated aluminium cans based on percentage assay and total impurities upon storage at T~0s Τ~1ϋϋ @ 40°C/75 % RH and 25°C/60 % RH and T-3M© 4S’C/75 % RH and 25°C/6U % RH.
Time % Assay (LG) % total impurities
initial time T ~ 0 99.9 <LoG
T~1M@ 25/60 100.6 <LoG
7- 1M @40/75 99.1 0.05
T = 3M @ 25/60 98.8 0.11
T = 3M @40/75 98.5 0.15
Table 11, Chemical stability of fluticasone propionate in HFA-134a in uncoated aluminium cans based on percentage assay and total impurities upon storage at T~0,
T«1M © 40KG/7S % RH and 25eC/60 % RH and Τ~3Μ@ 40°C/75 % RH and 25°C/60 % RH.
Time % Assay (LG) % total impurities
initial time T ~ 0 98.5 <LoQ
T = 1M @25/80 98.2 0.19
T~1M @40/75 97,8 0.38
T = 3M @ 25/60 94.8 0.58
T = 3M @40/75 93.8 0.69
Table 12, Chemical stability of fluticasone propionate in HFA-152a in unooatsd aluminium cans based on percentage assay arid total impurities upon storage at T~0, T~1M @ 4S°C/7S % RH and 25’C/80 % RH and T=3M@ 4Qce/?£
RH.
Time % Assay (LC) % total impurities
initial time T ~ 0 98.5 <LcQ
ϊ~ 1M @ 25/60 98.6 <LoQ
7 ~ 1M @40/75 98.4 Otoe
T ~ 3M @ 25/60 97.6 <LoQ
T 3M @40/75 97.2 0.58
It Gian: be seen from the data in Tables 7 to 12 above that giycopyrronium bromide, indaoateroi and fluticasone propionate all exhibit superior chemical .stability under accelerated test conditions when HFA-I52a is used as the aercsoltoation io propellant rather than HFA-134a.
1. A pharmaceuficai composition comprising:
(i) a drug component cdmprisingaf least one pharmeeeuficdliy aooeptable salt of g lyoopyrroiate:;: and (ii) a propellant component comprising 1 ,1~difiuoroethane (HFA-152a),
2. The pharmaceutical composition of claim 1, wherein the composition contains less than TOO ppm, preferably lessrthan 50 ppm:, mor© preferably less than:
m 10 ppm and especially less than 5 ppm of water based on the total weight of the p h arm aceuti cal: com positio n,
3, The pharmaceutical composition of claim 1 or 2, wherein the at least one pharmeceoticaliy acceptable salt of glycopyrrolate is glycopyrronlum bromide,
4, The pharmaceutical composition of any on© of the preceding claims., wherein the drug component additionally comprises at feast one long acting beta2-agonisf (LABA):.
2Q 5, The pharmaceutical composition of claim 4, wherein the at least one long acting heta-2-agonist is selected from fas group consisting of indacaterol, olodaferoi, formoterol, vlianterol and the pharmaceutically acceptable salts thereof,
6. The pharmaceutical composition of claim 5, wherein the at least one tong acting beta~2-egonist is selected from the group consisting of indacaterol and indacaterol maleate,
7. The pharmaceutical composition of any one of the preceding claims, wherein the drug component additionally comprises at least one corticosteroid.
8.,. The pharmaceutical composition of claim 7., wherein the at least one corticosteroid is selected from the group consisting of budesonide, mometasone. beciomethasone. fluticasone and the pharmaceutically acceptable salts thereof,
9, The pharmaceutical composition of claim 8, wherein the at least one corticosteroid is selected from the group consisting of budesonide, beclomethasone, beclomethasone dipropionafe, fluticasone furcate arid f I utl casone p repion a te.
19. The pharmaceutical composition of any one of the preceding claims, wherein the drug component comprises from 0.01 to 2.5 weight %, preferably from 0.01 to 2.0 weight %, more preferably from 0.05 to 2.0 weight % and especially from 0.05 to 1.5 weight % of the total weight of the pharmaceutical composition.
11. The pharmaceutical composition of any one of the preceding claims,

Claims (1)

  1. TO wherein the propellent component comprises from 80.0 to 99.99 weight %, preferably From 90.0 to 99,99 weight %, more preferably from 98.5 to 99,99 weight % and especially from 97.5 to 99.95 weight % of the total weight of the pharmaceutical composition.
    is 12. The pharmaceutical composition of any one of the preceding claims, wherein at least 90 weight %, preferably at least 95 weight % and more preferably at least 99 weight % of the propellent component is 1,1 -difiuoroethane (HFA-152a).
    13, The pharmaceutical composition of any one of claims 1 to 11, wherein the propellant component is entirely 1,1-difiuoroethane (HFA-152a),
    14. The pharmaceutical composition of any one of the preceding claims, wherein at least 95 weight %, preferably at least 98 weight % and more preferably at least 99 weight % of the composition consists of the two components (i) and (ii).
    15. i ho pharmaceutical composition of any one of the preceding claims further comprising a surfactant component composing at least one surfactant compound,
    16. The pharmaceutical composition of claim 15, wherein the surfactant component comprises at least one surfactant compound selected from polyvinylpyrrolidone, polyethylene glycol surfactants, oleic acid and lecithin.
    17. The pfiarmaceuticai composition of any one of the preceding claims further comprising a polar excipient.
    18, The pharmaceuticai composition of claim 17, wherein the paler excipient is ethanol.
    19, The pharmaceutical composition of any one of claims 1 to 16 which is free of polar excipients,
    20, The pharmaceutical composition of any one of claims 1 to 18 which is free of ethanol.
    21. j he pharmaceutical composition of any one of claims 1 to 13 which consists entirely of the two components (i) and (ii),
    22. The pharmaceutical composition of any one of claims 1 to 20 which is free of acid stabilisers.
    23. The pharmaceutical composition of any one of the preceding claims which after storage in uncoated aluminium containers at 25C and 60 % relative humidity for 3 months will produce less than 1,0 % by weight, preferably less than 0.8 % by weight and more preferably less than 0.6 % by weight of Impurities from the degradation of the at least one pharmaceutically acceptable salt of giycopyrrolafe based on the total weight of the at least one pharmaceuticaily acceptable salt of giycopyrrolafe and the impurities.
    24. The pharmaceutical composition of any one of the preceding claims which after storage in uncoated aluminium containers at 4Q°C and 75 % relative humidity for 3 months will produce less than 1.2 % by weight, preferably less than 1,0 % by weight and more preferably less than 0.8 % by weight of impurities from the degradation of the at least one pharmaceutically acceptable salt of giycopyrrolafe based or; the total weight of the at least one pharmaceutically acceptable salt of giycopyrrolafe and the impurities.
    25. The pharmaceutical composition of any one of the preceding claims, wherein at least 95.0 % by weight, preferably at least 95.0 % by weight and more preferably at least 97,0 % by weight of the at least one pharmaceutically acceptable salt of giycopyrrolafe that is contained originally in the pharmaceutical composition immediately following preparation will be present in the composition after storage in uncoated aluminium containers at 25°C and 60 % relative humidity tor 3 months and after storage in uncoated aluminium containers at 40'C and 75 % relative humidity for 3 months.
    26, The pharmaceutical composition of any one of claims 1 to 24, wherein at least 95,0 %. preferably at least 96,0 % and more preferably at least 97.0 % of the original pharmaceutical activity of the composition is retained after storage in uncoated aluminium containers at 25<:C and 60 % relative humidity for 3 months and after storage in uncoated aluminium containers at 40°C rind 75 % relative humidity for 3 months.
    27, The pharmaceutical composition of any one of the preceding claims which when delivered from a metered dose Inhaler yields a fine particle traction of the at least one pharmaceutically acceptable salt of giycopyrrolate which is at. least 35 weight %, preferably at least 40 weight % and more preferably at least 45 weight % of the emitted dose of the at least one pharmaceutically acceptable salt of glycepyrroiate.
    28. The pharmaceutical composition of any one of the preceding claims In the m form of a susoension.
    29. a solution.
    30. A sealed container that contains a pharmaceutical composition as claimed in any one of claims 1 to 29.
    31, The sealed container of claim 30 which is an uncoated aluminium can.
    32. The sealed container of claim 30 or claim 31 which is a pressurized aerosol container for use with a metered dose Inhaler (MDI).
    33. A metered dose inhaler (MDI) fitted with a sealed container as claimed in claim 32, .34, A method for treating: a patient suffering or likaiy to suffer from a respiratory disorder which: comprises administering to the patient a therapeutically or prophyiactically effective amount of a pharmeceuticai eomposition as claimed in any one of claims 1 to 29.
    35. The method of claim 34, wherein the respiratory disorder is asthma or a chronic obstructive pulmonary disease.
    36. The method of claim 34 or 35, wherein the pharmaceutical composition is delivered to the patient using: a metered dose: Inhaler (MDf),
    37. A method: of improving the stability ©f a pharmaceutical composition comprising a propellant component and a drug component comprising at least one pharmaceutically acceptable salt of giycopyrrolate, said method comprising using a propellant component comprising 1,1-dlfiuoroethane (HFA-152a).
    38. The method of claim 37, further comprising selecting the components and conditions for the preparation of the pharmaeeufieai .composition to malnialn the water content of the pharmaceutical composition below 100 ppm, preferably below 50 ppm, more preferably below 10 ppm and particularly below 5 p:p:m based on the total weight of the pharmaceutical composition.
    39. The method of claim 37 or 38, wherein the at least one pharmaceuticaily acceptable salt of giycopyrrolate is glycopyrronium bromide.
    40. The method of any one of claims 37 to 39. wherein the drug component additionally comprises at least one long acling beta-2-agonlst (LABA).
    41. The method of claim 40, wherein the at least one long acting beia-2-agonist is selected from the group consisting of indacateroi, olodateroi, formoteroi, viianterol and the pharmaceutically acceptable sails thereof.
    42. The method of claim 41, wherein the at least one long acting beta-2-agonist is selected from the group consisting of indacateroi and indacateroi maleate,
    43. I be method of any one of claims 37 to 42. wherein the drug component additionaliy comprises at least one corticosteroid.
    44. The method of claim 43, wherein the at least one corticosteroid is selected 5 from the group consisting of budesonide, mometasone, beolomethaso.ne, fluticasone and the pharmaceutically acceptable salts thereof,
    45. The method of claim 44, wherein the at least one corticosteroid is selected from the group consisting of budesonide, beclomethasone, beclomethasone
    W dipropionate, fluticasone furcate and fluticasone propionate.
    46. The method of any one of claims 37 to 45, wherein the drug component comprises from 0.01 to 2.5 weight %, preferably from 0.01 to 2.0 weight %, more preferably from 0.05 io 2.0 weight % and especially from 0.05 to 1.5 weight % of is the total weight of the pharmaceutical composition.
    47. The method of any one of claims 37 to 40, wherein the propellant component comprises from 80.0 to 99.99 weight %, preferably from 90.0 to 99.99 weight %, more preferably from 98.5 to 99,99 weight % and especially from 97.5 to 99.95 weight % of the total weight of the pharmaceutical composition.
    4-3. The method of any one of claims 37 to 47, wherein at least 90 weight preferably at least 95 weight % and more preferably at least 99 weight % of the propellant component is 1,1-difluoroethane (HFA-152a),
    49. The method of any one of claims 37 to 47, wherein the propellant component Is entirely 1 ,l~difiuoroethane (HFA-152a).
    50. The method of any one of claims 37 to 49, wherein at least 95 weight %. 30 preferably at least 98 weight % and more preferably at least 99 weight % of the pharmaceutical composition consists of the drug component and the propellant component.
    51. The method of any one of claims 37 to 50, wherein the pharmaceutical composition further comprises a surfactant component comprising at least one surfactant compound.
    52. The method of ciaim 51, wherein the surfactant component comprises at least one surfactant compound selected from polyvinylpyrrolidone, polyethylene glycol surtactants, oleic: acid and lecithin,
    53. The method of any one of claims 37 to 52 further comprising a polar excipient.
    54. The method of claim 53, wherein the polar excipient is ethanol.
    55. Tiie method of any one of claims 37 to 52, wherein the pharmaceutical composition is free of polar excipients.
    56. The method of any one of claims 37 to 52, wherein the pharmaceutical composition is free of ethanol.
    57. The method of any one of claims 37 to 49, wherein the pharmaceutical composition consists entirely of the drug component and the propellant component,
    68,: The method of any one of claims 37 to 57, wherein the pharmaceutical composition after storage In uncoated aluminium containers at 25“C and 60 % relative humidity for 3 months will produce less than 1.0 % by weight, preferably less than 0.8 % by weight and more preferably less than 0.6 % by weight of impurities from the degradation of the at least one pharmaceuticalfy acceptable salt of glycopyrrolate based on the totai weight of the at least one pharmaceutically acceptable salt of glycopyrrolate and the impurities.
    59, The method of any one of claims 37 to 58, wherein the pharmaceutical composition after storage in uncoated aluminium containers at 4Q°C ano 75 % relative humidity for 3 months will produce less than 1.2 % by weight, preferably less than 1,0 % by weight and more preferably less than 0.8 % by weight of impurities from the degradation of the at least one pharmaceutically acceptable salt of glycopyrrolate based on the total weight of the at least one pharmaceutically acceptable salt of glycopyrrolate and the impurities.
    3.5
    60. The method of any on© of claims 37 io 69, wherein af least 98,0 % by weight, preferably at least 96,0 % by weight and more preferably at least 97,0 % by weight of the at least one- pharmaeeuttcaliy acceptable salt or giycopyrrolafe that Ils contained originally in the pharmaceutical composition immediately following preparation wiIt be present in the composition after storage in uncoated aluminium containers at 2SC and; 6© % relative humidity for 3 months and after storage in uneoatod aluminium containers at 40O and 75 % relative humidity for 3 months.
    81, The method of any one of claims 37 to 53, wherein at least 95.0 %, preferably at least 98,0 % and more preferably at least 97,0 % of the original pharmaceutical activity of the composition is retained after storage in uncoated aluminium containers at. 25°C and 60 % relative humidity for 3 months and after storage In uncoated aluminium containers at 40°C and 75 % relative humidity for 3 months.
    62. The method of any one of claims 37 to 81, wherein the pharmaceutical composition is in the form of a suspension,
    83,. The method of any one of claims 37 to 81, wherein the pharmaceutteal composition is in the term of a solution.
    64, The method of any one of claims 37 to 83 which is free of acid stabilisers,
    65. A method of improving the aerosofeation performance of a pharmaceutical corn positlo n com prising a p ro pell a nt co mpo nent and a drug oom portent com p r is i n g at least one pharmaceutically acceptable salt of giycopyrrolate, said method comprising: using a propellant component comprising 1.1 -difluoroethane (HFA152a).
    86. The method of claim 85, wherein the method provides a pharmaceutical composition which when delivered from a metered dose inhaler yields a fine particle fraction of the at least one pharmaceutically acceptable salt of giycopyrrolate which is at least 35 weight %, preferably at least 40 weight % and more preferably at least 45 weight % of the emitted dose of the at least one pharmaceutically acceptable salt of giycopyrrolate.
    67, The method of claim 66:, wherein the fine particle fraction of the at least one pharmaceutically acceptable salt of glycopyrrotafe in the emitted dose Is at least 35 weight %, preferably at least 40 weight % and more preferably at least 45 weight % ef the emitted dose of the at least one pharmaceuticaliy acceptable salt of gtycopyrrolate after storage of the pharmaceutical composition for 1 month at 40°C and 75% relative humidity.
    68:. The method of any one of claims: 65 to 67, wherein the pharmaceutical composition is a composition as claimed in any one of claims 1 to 28 ;o
    69. The pharmaceutical composition of claim 1, wherein the drug component comprises glycopyrronium bromide, indaeaterol and fluticasone propionate and 'Be fine panicle fraction of each drug in the emitted dose when the pharmaceutical composition is delivered from a metered dose inhaler is at least: 35 weight: %, preferably at least 40 weight % and more preferably at least 45 weight % of the emitted dose of that druo
    70, The pharmaceutical' composition of claim 89, whereih the fine particle fractions of the glycopyrronium bromide, indaeaterol and fluticasone propionate in the emitted dose are observed after storage for 1 month at 40X and 75% relative humidity.
    71. : The pharmaceutical composition of claim 69 or 70, wherein the composition contains less than: 100 ppm, preferably less than 50 ppm, more preferably less than
    10 ppm and especially less than 5 ppm: of wafer based on the: total weight of the pharmaceutical composition,
    72. The pharmaceutical composition of any one of claims 69 to 71, wherein the drug component comprises from 0,01 to 2.5 weight %, preferably from 0.01 to 2,0 weight %, more preferably from 0.05 to 2.0 weight % and especially from 0.05 to 1,5 weight % of the total weight of the pharmaceutical composition,
    73. The pharmaceutical composition of any one of ciaims 69 to 72, wherein the propellant component comprises from: 80.0 to 99.99 weight %, preferably from 90.0 to 99.99 weight %, more preferably from 98.5 io 99,99 weight % and especially from 87,5 to 99,96 weight % of the total weight of the pharmaceutical composition.
    74. The pharmaceutical composition of any one of claims 89 Io. 73, wherein at least 90 weight preferably at least 95 weight % and mare preferably at least 99 weight % of the propellant component is i,1-difluoroethane (HFA-152a),
    75. The pharmaceutical composition of any one: of claims 69 to 73, wherein the propellant component is entirely 1,1 -difluoroethane (HFA-152a).
    76. The pharmaeeutieai composition of any one of claims 69 to 75, wherein at ,W least 95 weight: preferably at least 98 weight % and more preferably at least 99 weight % of the composition consists of the two components (i) and (ii).
    77. The pharmaceutical composition of any one of claims 69 to 76 further comprising a surfactant: component: oomphsing at least: one surfactant compound.
    78. The pharmaeeutieai composition of claim 77, wherein the surfactant component comprises at least: one surfactant compound: selected from: polyvinylpyrrolidone, polyethylene glycol surfactants, oleic acid and lecithin;
    79, The pharmaceutical composition of any one of claims 69 to 78 further comprising a polar excipient
    80, The pharmaeeutieai composition of oiaim 79, wherein the polar excipient is ethanol.
    2:5
    81, The pharmaceutical composition of any one of claims 89 to 78 which is free of polar excipients.
    82, The pharmaceutical composition of any one of claims; 89: to 75 which 30 consists entirely of the two components (i) and (ii).
    83, The pharmaceutical composition of any one of claims 69 to 81 which is free of acid stabilisers.
    Λχ<
    ytAjg/ZW»1
    Intellectual
    Property
    Office
    Application No: GB1615917.0 Examiner: Mr Robert Goodwill
    Claims searched: 1-83 Date of search: 25 May 2017
    Patents Act 1977: Search Report under Section 17
    Documents considered to be relevant:
    Category Relevant to claims Identity of document and passage or figure of particular relevance Y 1-83 WO 2012/110770 A2 (CIPLA LIMITED), see examples, particularly examples 1-12 Y 1-83 WO 2012/156711 Al (MEXICHEM AMANCO HOLDING), see EPO abstract AN GB2012051059-W and examples
    Categories:
    X Document indicating lack of novelty or inventive step A Document indicating technological background and/or state of the art. Y Document indicating lack of inventive step if combined with one or more other documents of same category. P Document published on or after the declared priority date but before the filing date of this invention. & Member of the same patent family E Patent document published on or after, but with priority date earlier than, the filing date of this application.
    Field of Search:
    Search of GB, EP, WO & US patent documents classified in the following areas of the UKCX :
    International Classification:
    Subclass Subgroup Valid From A61K 0031/40 01/01/2006 A61K 0009/00 01/01/2006 A61K 0047/06 01/01/2006 A61P 0011/12 01/01/2006 C07D 0207/12 01/01/2006
    Intellectual Property Office is an operating name of the Patent Office www.gov.uk/ipo
GB1615917.0A 2016-09-19 2016-09-19 Pharmaceutical composition Withdrawn GB2558191A (en)

Priority Applications (46)

Application Number Priority Date Filing Date Title
GB1615917.0A GB2558191A (en) 2016-09-19 2016-09-19 Pharmaceutical composition
UAA201902770A UA123919C2 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
JP2019515227A JP6781829B2 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
PCT/GB2017/052761 WO2018051130A1 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
PE2019000674A PE20191043A1 (en) 2016-09-19 2017-09-18 PHARMACEUTICAL COMPOSITION
MYPI2019001316A MY202069A (en) 2016-09-19 2017-09-18 Pharmaceutical composition
US16/334,158 US10888546B2 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
ES19199780T ES2968212T3 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
GEAP201715035A GEP20217239B (en) 2016-09-19 2017-09-18 Pharmaceutical composition
ES17777635T ES2892673T3 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
ES21183659T ES2957459T3 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
MX2021009476A MX392213B (en) 2016-09-19 2017-09-18 PHARMACEUTICAL COMPOSITIONS COMPRISING GLYCOPYRROLATE SALTS AND 1,1-DIFLUOROETHANE.
EP17777635.8A EP3515432B1 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
CN202210401223.3A CN114712338A (en) 2016-09-19 2017-09-18 pharmaceutical composition
EP21183659.8A EP3915555B1 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
AU2017328907A AU2017328907B2 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
CN201780057068.5A CN109789126B (en) 2016-09-19 2017-09-18 Pharmaceutical composition
ES19199783T ES2968453T3 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
EP19199780.8A EP3607936B1 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
MX2019003098A MX387723B (en) 2016-09-19 2017-09-18 PHARMACEUTICAL COMPOSITION COMPRISING GLYCOPYRRONIUM BROMIDE, FLUTICASONE PROPIONATE AND 1,1-DIFLUOROETHANE.
KR1020217021521A KR20210089273A (en) 2016-09-19 2017-09-18 Pharmaceutical composition
NZ752430A NZ752430B2 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
PH1/2019/500579A PH12019500579B1 (en) 2016-09-19 2017-09-18 Pharmaceutical composition
EP19199783.2A EP3610871B1 (en) 2016-09-19 2017-09-18 Pharmaceutical composition comprising glycopyrrolate
CN202210090188.8A CN114272238A (en) 2016-09-19 2017-09-18 Pharmaceutical composition
BR112019005133-3A BR112019005133B1 (en) 2016-09-19 2017-09-18 PHARMACEUTICAL COMPOSITION, METERED-DOSE INHALER, AND METHODS FOR IMPROVING THE CHEMICAL STABILITY OF A PHARMACEUTICAL COMPOSITION, AND FOR IMPROVING THE AEROSOL DISPERSION PERFORMANCE OF A PHARMACEUTICAL COMPOSITION
CN202210090190.5A CN114515284A (en) 2016-09-19 2017-09-18 Pharmaceutical composition
KR1020197010385A KR102277635B1 (en) 2016-09-19 2017-09-18 pharmaceutical composition
CA3037092A CA3037092C (en) 2016-09-19 2017-09-18 Stable pharmaceutical compositions comprising glycopyrrolate and 1,1-difluoroethane (hfa-152a) suitable for use in metered dose inhalers (mdis)
IL265360A IL265360B2 (en) 2016-09-19 2019-03-13 Pharmaceutical composition
MX2021009475A MX2021009475A (en) 2016-09-19 2019-03-15 Pharmaceutical composition.
SA519401336A SA519401336B1 (en) 2016-09-19 2019-03-17 Pharmaceutical composition
CONC2019/0002556A CO2019002556A2 (en) 2016-09-19 2019-03-19 Pharmaceutical composition
ZA2019/02053A ZA201902053B (en) 2016-09-19 2019-04-02 Pharmaceutical composition
US16/582,993 US11179366B2 (en) 2016-09-19 2019-09-25 Pharmaceutical composition
US16/582,973 US11103480B2 (en) 2016-09-19 2019-09-25 Pharmaceutical composition
JP2020040655A JP7041703B2 (en) 2016-09-19 2020-03-10 Pharmaceutical composition
AU2020202626A AU2020202626B2 (en) 2016-09-19 2020-04-17 Pharmaceutical composition
US17/361,851 US11826349B2 (en) 2016-09-19 2021-06-29 Pharmaceutical composition
US17/361,819 US11826348B2 (en) 2016-09-19 2021-06-29 Pharmaceutical composition
US17/361,772 US11642330B2 (en) 2016-09-19 2021-06-29 Pharmaceutical composition
AU2021205045A AU2021205045C1 (en) 2016-09-19 2021-07-14 Pharmaceutical composition
US17/467,778 US11690823B2 (en) 2016-09-19 2021-09-07 Pharmaceutical composition
JP2022022292A JP7228726B2 (en) 2016-09-19 2022-02-16 Pharmaceutical composition
US18/489,150 US20240050405A1 (en) 2016-09-19 2023-10-18 Pharmaceutical composition
US18/489,133 US20240050404A1 (en) 2016-09-19 2023-10-18 Pharmaceutical composition

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GB2558191A true GB2558191A (en) 2018-07-11

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WO2020249934A1 (en) * 2019-06-11 2020-12-17 Mexichem Fluor S.A. De C.V. Method for charging a container for use with a medication delivery apparatus, container for such an apparatus and method for treating a patient
CN113244490A (en) * 2020-01-28 2021-08-13 奇斯药制品公司 Pressurized metered dose inhalers comprising buffered pharmaceutical formulations
GB2597755A (en) * 2020-08-03 2022-02-09 Mexichem Fluor Sa De Cv Pharmaceutical composition
WO2024157282A1 (en) * 2023-01-24 2024-08-02 Cipla Limited Pharmaceutical compositions of green propellant

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WO2012156711A1 (en) * 2011-05-13 2012-11-22 Mexichem Amanco Holding S.A. De C.V. Pharmaceutical compositions

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Publication number Priority date Publication date Assignee Title
WO2020249934A1 (en) * 2019-06-11 2020-12-17 Mexichem Fluor S.A. De C.V. Method for charging a container for use with a medication delivery apparatus, container for such an apparatus and method for treating a patient
CN113905720A (en) * 2019-06-11 2022-01-07 墨西哥氟石股份公司 Method of filling a container for use with a drug delivery device, container for such a device and method for treating a patient
CN113244490A (en) * 2020-01-28 2021-08-13 奇斯药制品公司 Pressurized metered dose inhalers comprising buffered pharmaceutical formulations
GB2597755A (en) * 2020-08-03 2022-02-09 Mexichem Fluor Sa De Cv Pharmaceutical composition
WO2024157282A1 (en) * 2023-01-24 2024-08-02 Cipla Limited Pharmaceutical compositions of green propellant

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