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US20170056322A1 - Punctal plug with active agent - Google Patents

Punctal plug with active agent Download PDF

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Publication number
US20170056322A1
US20170056322A1 US15/247,574 US201615247574A US2017056322A1 US 20170056322 A1 US20170056322 A1 US 20170056322A1 US 201615247574 A US201615247574 A US 201615247574A US 2017056322 A1 US2017056322 A1 US 2017056322A1
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US
United States
Prior art keywords
active agent
punctal plug
medication
polymer
punctal
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.)
Abandoned
Application number
US15/247,574
Inventor
Steven A. Odrich
Liane C. Glazer
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.)
Mati Therapeutics Inc
Original Assignee
Mati Therapeutics Inc
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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35096541&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20170056322(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Mati Therapeutics Inc filed Critical Mati Therapeutics Inc
Priority to US15/247,574 priority Critical patent/US20170056322A1/en
Priority to US15/427,578 priority patent/US20170172916A1/en
Publication of US20170056322A1 publication Critical patent/US20170056322A1/en
Priority to US16/360,561 priority patent/US20200138701A9/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A61K9/0048—Eye, e.g. artificial tears
    • A61K9/0051—Ocular inserts, ocular implants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F9/00—Methods or devices for treatment of the eyes; Devices for putting in contact-lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand
    • A61F9/0008—Introducing ophthalmic products into the ocular cavity or retaining products therein
    • A61F9/0017—Introducing ophthalmic products into the ocular cavity or retaining products therein implantable in, or in contact with, the eye, e.g. ocular inserts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F9/00—Methods or devices for treatment of the eyes; Devices for putting in contact-lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand
    • A61F9/007—Methods or devices for eye surgery
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F9/00—Methods or devices for treatment of the eyes; Devices for putting in contact-lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand
    • A61F9/007—Methods or devices for eye surgery
    • A61F9/00772—Apparatus for restoration of tear ducts
    • 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
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A61K38/13—Cyclosporins

Definitions

  • the present invention relates generally to the field of medicine, and in particular to a new and useful method and apparatus for administering an active agent, i.e. a medicine or medication, to a subject by transdermal or other surface absorption of the agent into the tissues in and around one or both eyes of the subject.
  • an active agent i.e. a medicine or medication
  • Punctal plugs are known which are made in suitable dimensions and of suitable materials to be removably inserted into the upper and/or lower punctal apertures or punctum of the eye, to block the opening and the canaliculus communicating therewith, to prevent drainage of lacrimal fluid (tears).
  • Such plugs are known to be made of suitable materials, such as polymers, for example polytetrafluorethylene (known by the trademark TEFLON), or hydroxyethylmethacrylate (HEMA), hydrophilic polymer, methyl methacrylate, or silicon, or even of stainless steel or other inert metal material.
  • an active agent such as nicotine or a birth control drug
  • a patch which can be worn against the skin of a subject for transdermally administering the active agent to the subject.
  • an ocular implant such as a punctal plug
  • the active agent or drug is meant for treating the tissues at the walls of the canaliculus, for example, the drug is applied only to inner surfaces of the plug that are adapted to be in contact with or near the tissues of the canaliculus.
  • the presence of tears is highly advantageous as a natural vehicle or carrier for the agent.
  • the active agent or drug is meant for treating the eye itself, the drug is applied only to outer surfaces of the implant or plug that are adapted to be outside the canaliculus.
  • the presence of previously secreted tears or a tear pool is again advantageous as a natural vehicle or carrier for the agent.
  • Any or all surfaces of the implant may carry the active agent there the desire is simply to have the agent enter the subjects blood stream via the tissues in and around the eye.
  • FIG. 1 is a schematic perspective view of an ocular implant in the form of a punctal plug according to the present invention.
  • FIG. 2 is a perspective view of the area around the eye with other embodiments of the invention.
  • FIG. 1 shows a punctal plug generally designated 10 , having a stem 12 for insertion into the punctal aperture 20 of an eye 24 , and along the canaliculus 22 communicating with the aperture.
  • Plug 10 has a large stopper structure 14 connected to the outer end of stem 12 for seating against the aperture 20 and sealing the canaliculus 22 against the flow of tears onto the surface of the eye or eyeball 24 .
  • FIG. 2 illustrates an eye 24 communicating with upper and lower canaliculi 22 a and 22 b, each with their our implant 10 a and 10 b.
  • Implant 10 a is a substantially cylindrical and solid collagen plug that has been inserted into the upper punctum or tear duct 20 a, to block the flow of tears while lower implant 10 b is hollow like a straw for the passage of tears.
  • Implant 10 b includes a tapered shaft or stem 12 a with a flared open end 12 b immobilized at the lower punctum 20 b.
  • a mushroom shaped inner stopper 14 a is formed at the opposite end of shaft 12 a for further setting the location of the implant in the tear duct.
  • One of the embodiments illustrated in FIG. 2 may include a hollow core of the plug and another, e.g. the lower one, may include a hollow core filled with medication.
  • the active agent e.g. a medicine or medication is applied, e.g. in one or more bands of polymer material 16 at the inner end of the stem, or at 18 on the outer end of the stopper 14 in the embodiment of FIG. 1 , or over some or all of the surfaces of the implants of FIG. 2 , or otherwise.
  • Polymer that is absorbent to the agent is preferable so that sufficient agent is present and available for discharge into the surrounding tissues.
  • a porous or absorbent material can alternatively be used to make up the entire plug or implant which can be saturated with the active agent.
  • the hollow implant 10 b of FIG. 2 is also particularly useful in that the active agent can be applied to, or is otherwise available at the inner surface or interior of the implant, and is uniquely structured to pass tears and thus administer the active agent to the tear stream in a fashion that is controlled by the flow of tears which thus act as the carrier for the agent.
  • the hollow implant of the present invention provides a very different drug administering method, scheme and structure.
  • Non-limiting examples of the active agents or medications which are appropriate for use with the invention include, for example only: topical prostaglandin derivatives such as latanoprost, travaprost and bimataprost used for the topical treatment of glaucoma. Also a treatment for corneal infections is appropriate using ciprofloxacin, moxifloxacin or gatifloxacin.
  • Systemic medications useful for this invention are those used for hypertension such as atenolol, nifedipine or hydrochlorothiazide. Any other chronic disease requiring chronic medication could be used.
  • allergic conjunctivitis and rhinitis are also good applications for the invention, e.g. using antihistamine and anti-allergy medication such as olopatadine and cromalyn sodium in or on the implant.
  • active agents are not comprehensive in that many other agents can be used with the present invention.
  • a treatment for dry eye by topical cyclosporin is particularly interesting for administration by the present invention, but many other active agents can also be administered using the method and apparatus of the invention.
  • the invention is meant to embody all implants or devices which are implanted into the eye-lid canalicular puncta of the naso-lacrimal system with the goal of delivering drug to the eye or to the body.
  • the implant is inserted into either the inferior (lower) or superior (upper) punctum or possibly both.
  • the apparatus is constructed so as to have a drug attached to one or both sides of the implant and an occlusive plug of some inert biocompatible material.
  • the implant could be oriented in the punctal canal to deliver the drug either to the tear lake and thus the eye, or to the nasolacrimal system and thus the body's systemic circulation.
  • the drawings illustrate only three embodiments of the punctal plug or implant delivery system of the invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Surgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Prostheses (AREA)

Abstract

A method and apparatus for administering an active agent such as a medicine to a subject, uses an ocular implant such as a punctal plug, to which the active agent has been applied. The implant is installed at the eye of the subject for administering the active agent via tissues of the eye.

Description

    FIELD AND BACKGROUND OF THE INVENTION
  • The present invention relates generally to the field of medicine, and in particular to a new and useful method and apparatus for administering an active agent, i.e. a medicine or medication, to a subject by transdermal or other surface absorption of the agent into the tissues in and around one or both eyes of the subject.
  • Punctal plugs are known which are made in suitable dimensions and of suitable materials to be removably inserted into the upper and/or lower punctal apertures or punctum of the eye, to block the opening and the canaliculus communicating therewith, to prevent drainage of lacrimal fluid (tears). Such plugs are known to be made of suitable materials, such as polymers, for example polytetrafluorethylene (known by the trademark TEFLON), or hydroxyethylmethacrylate (HEMA), hydrophilic polymer, methyl methacrylate, or silicon, or even of stainless steel or other inert metal material.
  • It is also known to apply an active agent such as nicotine or a birth control drug, to the inner surface of a patch which can be worn against the skin of a subject for transdermally administering the active agent to the subject.
    • SUMMARY OF THE INVENTION
  • It is an object of the present invention to provide a method and an apparatus for administering an active agent to a subject by applying the active agent to at least one surface of an ocular implant such as a punctal plug, and installing the implant, e.g. inserting the punctal plug into a punctal aperture of the subject.
  • If the active agent or drug is meant for treating the tissues at the walls of the canaliculus, for example, the drug is applied only to inner surfaces of the plug that are adapted to be in contact with or near the tissues of the canaliculus. The presence of tears is highly advantageous as a natural vehicle or carrier for the agent.
  • If the active agent or drug is meant for treating the eye itself, the drug is applied only to outer surfaces of the implant or plug that are adapted to be outside the canaliculus. Here the presence of previously secreted tears or a tear pool is again advantageous as a natural vehicle or carrier for the agent.
  • Any or all surfaces of the implant may carry the active agent there the desire is simply to have the agent enter the subjects blood stream via the tissues in and around the eye.
  • The various features of novelty which characterize the invention are pointed out with particularity in the claims annexed to and forming a part of this disclosure. For a better understanding of the invention, its operating advantages and specific objects attained by its uses, reference is made to the accompanying drawings and descriptive matter in which preferred embodiments of the invention are illustrated.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • In the drawings:
  • FIG. 1 is a schematic perspective view of an ocular implant in the form of a punctal plug according to the present invention; and
  • FIG. 2 is a perspective view of the area around the eye with other embodiments of the invention.
    •  DESCRIPTION OF THE PREFERRED EMBODIMENT
  • Referring now to the drawing, FIG. 1 shows a punctal plug generally designated 10, having a stem 12 for insertion into the punctal aperture 20 of an eye 24, and along the canaliculus 22 communicating with the aperture.
  • Plug 10 has a large stopper structure 14 connected to the outer end of stem 12 for seating against the aperture 20 and sealing the canaliculus 22 against the flow of tears onto the surface of the eye or eyeball 24.
  • FIG. 2, where the same of similar numerals are used to designate functionally similar parts, illustrates an eye 24 communicating with upper and lower canaliculi 22 a and 22 b, each with their our implant 10 a and 10 b. Implant 10 a is a substantially cylindrical and solid collagen plug that has been inserted into the upper punctum or tear duct 20 a, to block the flow of tears while lower implant 10 b is hollow like a straw for the passage of tears. Implant 10 b includes a tapered shaft or stem 12 a with a flared open end 12 b immobilized at the lower punctum 20 b. A mushroom shaped inner stopper 14 a is formed at the opposite end of shaft 12 a for further setting the location of the implant in the tear duct.
  • One of the embodiments illustrated in FIG. 2, e.g. the upper implant, may include a hollow core of the plug and another, e.g. the lower one, may include a hollow core filled with medication.
  • The active agent, e.g. a medicine or medication is applied, e.g. in one or more bands of polymer material 16 at the inner end of the stem, or at 18 on the outer end of the stopper 14 in the embodiment of FIG. 1, or over some or all of the surfaces of the implants of FIG. 2, or otherwise. Polymer that is absorbent to the agent is preferable so that sufficient agent is present and available for discharge into the surrounding tissues. A porous or absorbent material can alternatively be used to make up the entire plug or implant which can be saturated with the active agent.
  • The hollow implant 10 b of FIG. 2 is also particularly useful in that the active agent can be applied to, or is otherwise available at the inner surface or interior of the implant, and is uniquely structured to pass tears and thus administer the active agent to the tear stream in a fashion that is controlled by the flow of tears which thus act as the carrier for the agent. Unlike the usual tear stopping punctal plug, the hollow implant of the present invention provides a very different drug administering method, scheme and structure.
  • Non-limiting examples of the active agents or medications which are appropriate for use with the invention include, for example only: topical prostaglandin derivatives such as latanoprost, travaprost and bimataprost used for the topical treatment of glaucoma. Also a treatment for corneal infections is appropriate using ciprofloxacin, moxifloxacin or gatifloxacin. Systemic medications useful for this invention are those used for hypertension such as atenolol, nifedipine or hydrochlorothiazide. Any other chronic disease requiring chronic medication could be used.
  • The treatment of allergic conjunctivitis and rhinitis are also good applications for the invention, e.g. using antihistamine and anti-allergy medication such as olopatadine and cromalyn sodium in or on the implant.
  • The advantage is that there would be no need for chronic pill-taking or drop taking. A once-per 3-6 month visit to the eye doctor would be all that is needed. Also the issue of non-compliance, a major impediment to successful treatment, would by avoided by the invention.
  • This list of active agents is not comprehensive in that many other agents can be used with the present invention. For example, a treatment for dry eye by topical cyclosporin is particularly interesting for administration by the present invention, but many other active agents can also be administered using the method and apparatus of the invention.
  • The invention is meant to embody all implants or devices which are implanted into the eye-lid canalicular puncta of the naso-lacrimal system with the goal of delivering drug to the eye or to the body.
  • The implant is inserted into either the inferior (lower) or superior (upper) punctum or possibly both. The apparatus is constructed so as to have a drug attached to one or both sides of the implant and an occlusive plug of some inert biocompatible material.
  • Depending on the desired therapy, the implant could be oriented in the punctal canal to deliver the drug either to the tear lake and thus the eye, or to the nasolacrimal system and thus the body's systemic circulation. The drawings illustrate only three embodiments of the punctal plug or implant delivery system of the invention.
  • While a specific embodiment of the invention has been shown and described in detail to illustrate the application of the principles of the invention, it will be understood that the invention may be embodied otherwise without departing from such principles.

Claims (20)

1-19. (canceled)
20. A method for administering an active agent to a subject using a punctal plug, the method comprising:
inserting the punctal plug into a punctal aperture of the subject, wherein the composition of the punctal plug comprises:
a) an active agent, and
b) a polymer,
wherein the shape of the punctal plug consists of a constant diameter cylinder configured to be inserted into a canalicular puncta of the subject.
21. The method of claim 20, wherein the active agent is selected from the group consisting of topical prostaglandin; latanoprost; travoprost; bimatoprost; a medication for treatment of a corneal infection; ciprofloxacin; moxifloxacin; gatifloxacin; a systemic medication; a medication for treating hypertension; atenolol; nifedipine; hydrochlorothiazide; and a medication for treating allergic conjunctivitistopical prostaglandin is latanoprost.
22. The method of claim 20, wherein the active agent is cyclosporine.
23. The method of claim 20, wherein the active agent is a medication for treatment of dry eye.
24. The method of claim 20, wherein the active agent is a medication for the topical treatment of glaucoma or corneal infection.
25. The method of claim 20, wherein the polymer is a hydrophilic polymer.
26. The method of claim 20, wherein the polymer is porous or absorbent.
27. A punctal plug comprising:
a) an active agent, and
b) a polymer,
wherein the shape of the punctal plug consists of a constant diameter cylinder configured to be inserted into a canalicular puncta of the subject.
28. The punctal plug of claim 27, wherein the active agent is cyclosporine.
29. The punctal plug of claim 27, wherein the active agent is a medication for treatment of dry eye.
30. The punctal plug of claim 27, wherein the active agent is a medication for the topical treatment of glaucoma or corneal infection.
31. The punctal plug of claim 27, wherein the polymer is a hydrophilic polymer.
32. The punctal plug of claim 27, wherein the polymer is porous or absorbent.
33. A punctal plug comprising:
a) an active agent,
b) a polymer, and
c) a hollow core filled with the active agent.
34. The punctal plug of claim 33, wherein the active agent is cyclosporine.
35. The punctal plug of claim 33, wherein the active agent is a medication for treatment of dry eye.
36. The punctal plug of claim 33, wherein the active agent is a medication for the topical treatment of glaucoma or corneal infection.
37. The punctal plug of claim 33, wherein the polymer is silicone.
38. The punctal plug of claim 33, wherein the polymer is porous or absorbent.
US15/247,574 2004-04-15 2016-08-25 Punctal plug with active agent Abandoned US20170056322A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US15/247,574 US20170056322A1 (en) 2004-04-15 2016-08-25 Punctal plug with active agent
US15/427,578 US20170172916A1 (en) 2004-04-15 2017-02-08 Punctal plug with active agent
US16/360,561 US20200138701A9 (en) 2004-04-15 2019-03-21 Punctal Plug With Active Agent

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10/825,047 US20050232972A1 (en) 2004-04-15 2004-04-15 Drug delivery via punctal plug
US12/604,202 US20100040670A1 (en) 2004-04-15 2009-10-22 Drug delivery via ocular implant
US13/533,676 US20120277694A1 (en) 2004-04-15 2012-06-26 Punctal plug with active agent
US14/472,844 US9463114B2 (en) 2004-04-15 2014-08-29 Punctal plug with active agent
US15/247,574 US20170056322A1 (en) 2004-04-15 2016-08-25 Punctal plug with active agent

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US14/472,844 Continuation US9463114B2 (en) 2004-04-15 2014-08-29 Punctal plug with active agent

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/427,578 Continuation US20170172916A1 (en) 2004-04-15 2017-02-08 Punctal plug with active agent

Publications (1)

Publication Number Publication Date
US20170056322A1 true US20170056322A1 (en) 2017-03-02

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Family Applications (7)

Application Number Title Priority Date Filing Date
US10/825,047 Abandoned US20050232972A1 (en) 2004-04-15 2004-04-15 Drug delivery via punctal plug
US12/604,202 Abandoned US20100040670A1 (en) 2004-04-15 2009-10-22 Drug delivery via ocular implant
US13/533,676 Abandoned US20120277694A1 (en) 2004-04-15 2012-06-26 Punctal plug with active agent
US14/472,844 Expired - Lifetime US9463114B2 (en) 2004-04-15 2014-08-29 Punctal plug with active agent
US15/247,574 Abandoned US20170056322A1 (en) 2004-04-15 2016-08-25 Punctal plug with active agent
US15/427,578 Abandoned US20170172916A1 (en) 2004-04-15 2017-02-08 Punctal plug with active agent
US16/360,561 Abandoned US20200138701A9 (en) 2004-04-15 2019-03-21 Punctal Plug With Active Agent

Family Applications Before (4)

Application Number Title Priority Date Filing Date
US10/825,047 Abandoned US20050232972A1 (en) 2004-04-15 2004-04-15 Drug delivery via punctal plug
US12/604,202 Abandoned US20100040670A1 (en) 2004-04-15 2009-10-22 Drug delivery via ocular implant
US13/533,676 Abandoned US20120277694A1 (en) 2004-04-15 2012-06-26 Punctal plug with active agent
US14/472,844 Expired - Lifetime US9463114B2 (en) 2004-04-15 2014-08-29 Punctal plug with active agent

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US15/427,578 Abandoned US20170172916A1 (en) 2004-04-15 2017-02-08 Punctal plug with active agent
US16/360,561 Abandoned US20200138701A9 (en) 2004-04-15 2019-03-21 Punctal Plug With Active Agent

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Cited By (1)

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US9463114B2 (en) 2016-10-11
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US20190216727A1 (en) 2019-07-18
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US20170172916A1 (en) 2017-06-22
US20120277694A1 (en) 2012-11-01

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