US20180028663A1 - Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug - Google Patents

Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug Download PDF

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Publication number
US20180028663A1
US20180028663A1 US15/660,924 US201715660924A US2018028663A1 US 20180028663 A1 US20180028663 A1 US 20180028663A1 US 201715660924 A US201715660924 A US 201715660924A US 2018028663 A1 US2018028663 A1 US 2018028663A1
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composition
active agent
adhesive
drug reservoir
transdermal patch
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US15/660,924
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Inventor
Eun Soo Lee
Parminder Singh
Appala Sagi
Amit K. Jain
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Corium LLC
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Corium International Inc
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Priority to US15/660,924 priority Critical patent/US20180028663A1/en
Assigned to CORIUM INTERNATIONAL, INC. reassignment CORIUM INTERNATIONAL, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SINGH, PARMINDER, JAIN, AMIT K., LEE, EUN SOO, SAGI, APPALA
Publication of US20180028663A1 publication Critical patent/US20180028663A1/en
Assigned to CORIUM, INC. reassignment CORIUM, INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: CORIUM INTERNATIONAL, INC.
Priority to US17/065,302 priority patent/US20210015761A1/en
Assigned to HERCULES CAPITAL, INC., AS AGENT reassignment HERCULES CAPITAL, INC., AS AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CORIUM, INC.
Assigned to CORIUM, LLC reassignment CORIUM, LLC CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: CORIUM, INC.
Assigned to COLUMBUS INVESTMENT HOLDINGS SA reassignment COLUMBUS INVESTMENT HOLDINGS SA INTELLECTUAL PROPERTY SECURITY AGREEMENT Assignors: CORIUM, LLC
Priority to US18/922,900 priority patent/US20250325496A1/en
Priority to US19/223,763 priority patent/US20250375396A1/en
Abandoned legal-status Critical Current

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Definitions

  • compositions, devices, and methods for transdermal administration of amine active agents provided in their salt form instead of neutral form amine active agents provided in their salt form instead of neutral form.
  • Amine drugs exist in two forms, a free base and a salt.
  • the salt form is the conjugated acid salt (i.e., protonated form) of an amine drug
  • the free base is the conjugated base (i.e., deprotonated form) of the amine drug.
  • the salt form is more stable, water soluble, and bioavailable than the free base form.
  • most oral formulations of amine drugs include the salt form of the amine drug.
  • transdermal formulations typically use a free base form because the free base is much more skin permeable than the salt form.
  • the composition comprises between about 0.5-35% w/w of sodium bicarbonate.
  • the composition comprises up to 20% w/w of the neutral form solubilizer.
  • the composition comprises up to 25% w/w of the matrix modifying additive.
  • a transdermal patch comprising a composition as described herein as a first drug reservoir and a backing layer.
  • the backing layer is an occlusive polymer film.
  • the transdermal patch comprises a nonwoven tie layer between the drug reservoir and the contact adhesive layer.
  • a method for treating Alzheimer's disease, Parkinson's disease, restless leg syndrome, attention deficit hyperactivity disorder, narcolepsy, depression, anxiety disorder, obsessive compulsive disorder, benign prostatic hyperplasia, acute urinary retention, opioid dependence, moderate acute pain in non-opioid-tolerant individuals, or moderate chronic pain are provided.
  • the method comprises providing a composition or a transdermal patch as described herein to a patient in need thereof.
  • Exemplary amine salt drugs include, but are not limited to, donepezil, memantine, rotigotine, ropinirole, rivastigmine, tamsulosin, methylphenidate, buprenorphine, fentanyl, fingolimod, and oxybutynin.
  • an adhesive matrix comprises about 0-25 wt %, about 0-20 wt %, about 0-15 wt %, about 0-10 wt %, about 0-5 wt %, about 5-25 wt %, about 5-20 wt %, about 5-15 wt %, about 5-10 wt %, about 10-25 wt %, about 10-20 wt %, about 10-15 wt %, about 15-25 wt %, about 15-20 wt %, or about 20-25 wt % of at least one adhesive matrix modifying additive.
  • FIG. 2 shows an exemplary transdermal patch 10 comprising a backing layer 12 , multiple drug reservoirs 14 , 16 separated by a nonwoven tie layer 18 , a rate-controlling membrane 20 , a contact adhesive layer 22 , and a release liner 24 .
  • This particular example presents multiple drug reservoirs separated by a tie layer, but in some embodiments, multiple adhesive drug reservoir layers may be in direct contact with each other without a tie layer.
  • each drug reservoir may comprise the same or different active agents.
  • each drug reservoir may comprise different concentrations of the same active agent.
  • the drug reservoir generally comprises a salt form of an active ingredient(s) (total 5-35% w/w), at least one salt form solubilizer (total 0-15% w/w), at least one neutral form solubilizer (total 0-15% w/w), at least one proton accepting entity a (total 0.5-30% w/w), matrix modifying additives (total 0-25% w/w), and optionally adhesive polymers (total 0-65% w/w).
  • the drug reservoir comprises any of the compositions for transdermal delivery described herein, e.g., in the Examples and in Section II.A.
  • the tie layer comprises a nonwoven fabric and does not comprise a rate controlling polymer membrane. In some embodiments, a tie layer comprises a rate controlling polymer membrane and does not comprise a nonwoven fabric. In some embodiments, a tie layer comprises both a nonwoven fabric and a rate controlling polymer membrane. To give but one example, a nonwoven fabric 18 and a rate controlling polymer membrane 20 may both be used when the tie layer is embedded within the drug reservoir ( 14 , 16 ) to help improve drug reservoir cohesion (see, e.g., FIG. 2 ).
  • the delivery system provides an in vitro skin flux of an active agent between about 0.5-100 ⁇ g/cm 2 -hr for a period of at least about 2 days.
  • the delivery system provides an in vitro skin flux of an active agent between about 0.5-80 ⁇ g/cm 2 -hr, 1-80 ⁇ g/cm 2 -hr, 2-80 ⁇ g/cm 2 -hr, 2-50 ⁇ g/cm 2 -hr, 4-50 ⁇ g/cm 2 -hr, 4-30 ⁇ g/cm 2 -hr, 0.5-15 ⁇ g/cm 2 -hr, 1-15 ⁇ g/cm 2 -hr or 4-15 ⁇ g/cm 2 -hr for a period of at least about 1 day, about 2 days, about 3 days, or about 4 days.
  • compositions as described herein comprising rotigotine (NEUPRO®) as an active agent are used for treating Parkinson's disease and restless leg syndrome, e.g., through administration of rotigotine by a transdermal patch.
  • Contemplated daily doses of rotigotine are 1 mg, 2 mg, 3 mg, 4 mg, 6 mg, and 8 mg, with a range of daily dose from about 0.5-10 mg and about 1-8 mg.
  • compositions as described herein comprising ropinirole (REQUIP®, REPREVE®, RONIROL®, ADARTREL®) as an active agent are used for treating Parkinson's disease and restless leg syndrome, e.g., through administration of ropinirole by a transdermal patch.
  • Contemplated daily doses of ropinirole are of 0.25 mg, 0.5 mg, 1 mg, 2 mg, 3 mg, 4 mg, 5 mg, 6 mg, 8 mg, and 12 mg, with a range of daily dose from about 0.1-15 mg and about 0.25-15 mg.
  • compositions as described herein comprising rivastigmine (EXELON®) as an active agent are used for treating Alzheimer's disease and/or Parkinson's disease dementia, e.g., through administration of rivastigmine by a transdermal patch.
  • Contemplated daily doses of rivastigmine are 1.5 mg, 2.0 mg, 3.0 mg, 4.5 mg, 4.6 mg, 6.0 mg, 9.0 mg, 9.5 mg, and 13.3 mg, with a range of daily dose from about 0.5-18 mg, about 1-15 mg and about 1.5-13.3 mg.
  • compositions as described herein comprising tamsulosin (FLOMAX®) as an active agent are used for treating benign prostatic hyperplasia, acute urinary retention, passage of kidney stones, e.g., through administration of tamsulosin by a transdermal patch.
  • Contemplated daily doses of tamsulosin are 0.4 mg and 0.5 mg, with a range of daily dose from about 0.1-1.0 mg, about 0.2-0.8 mg and about 0.4-0.5 mg.
  • Dermatomed human cadaver skin was obtained from a skin bank and frozen until ready for use. The skin was placed in water at 60° C. for 1-2 minutes after thawing and the epidermis carefully separated from dermis. The epidermis was either used immediately or wrapped and frozen for later use.
  • FIG. 4 depicts the design of the patch described in the comparative example.

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US17/065,302 US20210015761A1 (en) 2016-07-27 2020-10-07 Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug
US18/922,900 US20250325496A1 (en) 2016-07-27 2024-10-22 Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug
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US201762444745P 2017-01-10 2017-01-10
US201762457794P 2017-02-10 2017-02-10
US201762504391P 2017-05-10 2017-05-10
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US15/660,943 Active US9993466B2 (en) 2016-07-27 2017-07-26 Donepezil transdermal delivery system
US15/660,939 Active US10300025B2 (en) 2016-07-27 2017-07-26 Donepezil transdermal delivery system
US15/957,858 Active US10307379B2 (en) 2016-07-27 2018-04-19 Donepezil transdermal delivery system
US16/392,513 Active 2037-08-08 US11103463B2 (en) 2016-07-27 2019-04-23 Methods for treating alzheimer's disease with donepezil transdermal system
US16/392,544 Abandoned US20190247321A1 (en) 2016-07-27 2019-04-23 Donepezil transdermal delivery system
US17/065,302 Abandoned US20210015761A1 (en) 2016-07-27 2020-10-07 Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug
US17/395,359 Abandoned US20220016045A1 (en) 2016-07-27 2021-08-05 Methods for treating alzheimer's disease with donepezil transdermal system
US18/337,974 Abandoned US20240156747A1 (en) 2016-07-27 2023-06-20 Methods for treating alzheimer's disease with donepezil transdermal system
US18/922,900 Pending US20250325496A1 (en) 2016-07-27 2024-10-22 Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug
US19/085,857 Pending US20250375395A1 (en) 2016-07-27 2025-03-20 Transdermal formulation and delivery method of low solubility or unstable unionized neutral drugs by in situ salt-to-neutral drug conversion of salt drug
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US15/660,939 Active US10300025B2 (en) 2016-07-27 2017-07-26 Donepezil transdermal delivery system
US15/957,858 Active US10307379B2 (en) 2016-07-27 2018-04-19 Donepezil transdermal delivery system
US16/392,513 Active 2037-08-08 US11103463B2 (en) 2016-07-27 2019-04-23 Methods for treating alzheimer's disease with donepezil transdermal system
US16/392,544 Abandoned US20190247321A1 (en) 2016-07-27 2019-04-23 Donepezil transdermal delivery system
US17/065,302 Abandoned US20210015761A1 (en) 2016-07-27 2020-10-07 Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug
US17/395,359 Abandoned US20220016045A1 (en) 2016-07-27 2021-08-05 Methods for treating alzheimer's disease with donepezil transdermal system
US18/337,974 Abandoned US20240156747A1 (en) 2016-07-27 2023-06-20 Methods for treating alzheimer's disease with donepezil transdermal system
US18/922,900 Pending US20250325496A1 (en) 2016-07-27 2024-10-22 Sodium bicarbonate in situ conversion driven transdermal delivery of amine drug
US19/085,857 Pending US20250375395A1 (en) 2016-07-27 2025-03-20 Transdermal formulation and delivery method of low solubility or unstable unionized neutral drugs by in situ salt-to-neutral drug conversion of salt drug
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