CA2800716C - Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith - Google Patents
Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith Download PDFInfo
- Publication number
- CA2800716C CA2800716C CA2800716A CA2800716A CA2800716C CA 2800716 C CA2800716 C CA 2800716C CA 2800716 A CA2800716 A CA 2800716A CA 2800716 A CA2800716 A CA 2800716A CA 2800716 C CA2800716 C CA 2800716C
- Authority
- CA
- Canada
- Prior art keywords
- piroxicam
- matrix
- self
- adhesive
- patch
- 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.)
- Expired - Fee Related
Links
- 239000011159 matrix material Substances 0.000 claims abstract description 541
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims abstract description 278
- 229960002702 piroxicam Drugs 0.000 claims abstract description 278
- 208000002193 Pain Diseases 0.000 claims abstract description 133
- 206010061218 Inflammation Diseases 0.000 claims abstract description 70
- 230000004054 inflammatory process Effects 0.000 claims abstract description 68
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 62
- 230000001154 acute effect Effects 0.000 claims abstract description 62
- 208000005298 acute pain Diseases 0.000 claims abstract description 62
- 208000025978 Athletic injury Diseases 0.000 claims abstract description 4
- 230000006378 damage Effects 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims description 374
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 114
- 229920006243 acrylic copolymer Polymers 0.000 claims description 97
- 239000004264 Petrolatum Substances 0.000 claims description 93
- 229940066842 petrolatum Drugs 0.000 claims description 93
- 235000019271 petrolatum Nutrition 0.000 claims description 93
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 90
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 89
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 88
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 88
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 88
- 229920002313 fluoropolymer Polymers 0.000 claims description 85
- 239000004811 fluoropolymer Substances 0.000 claims description 85
- 229920006267 polyester film Polymers 0.000 claims description 85
- 239000002904 solvent Substances 0.000 claims description 74
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 61
- 230000035515 penetration Effects 0.000 claims description 61
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 57
- 239000004745 nonwoven fabric Substances 0.000 claims description 56
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 36
- 238000001704 evaporation Methods 0.000 claims description 30
- 230000008020 evaporation Effects 0.000 claims description 30
- 238000011200 topical administration Methods 0.000 claims description 11
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 9
- 210000001513 elbow Anatomy 0.000 claims description 3
- 210000003127 knee Anatomy 0.000 claims description 3
- 208000036487 Arthropathies Diseases 0.000 claims description 2
- 208000025940 Back injury Diseases 0.000 claims description 2
- 206010006811 Bursitis Diseases 0.000 claims description 2
- 206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 claims description 2
- 208000034656 Contusions Diseases 0.000 claims description 2
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 2
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 208000012659 Joint disease Diseases 0.000 claims description 2
- 208000008930 Low Back Pain Diseases 0.000 claims description 2
- 208000036631 Metastatic pain Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 2
- 208000004550 Postoperative Pain Diseases 0.000 claims description 2
- 208000026137 Soft tissue injury Diseases 0.000 claims description 2
- 208000010040 Sprains and Strains Diseases 0.000 claims description 2
- 208000000491 Tendinopathy Diseases 0.000 claims description 2
- 206010043255 Tendonitis Diseases 0.000 claims description 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
- 208000002849 chondrocalcinosis Diseases 0.000 claims description 2
- 230000009519 contusion Effects 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 210000002832 shoulder Anatomy 0.000 claims description 2
- 201000004415 tendinitis Diseases 0.000 claims description 2
- 210000000707 wrist Anatomy 0.000 claims description 2
- 229940079593 drug Drugs 0.000 abstract description 37
- 239000003814 drug Substances 0.000 abstract description 37
- 238000000034 method Methods 0.000 abstract description 36
- 230000036407 pain Effects 0.000 abstract description 9
- 230000000699 topical effect Effects 0.000 abstract description 9
- 230000000202 analgesic effect Effects 0.000 abstract description 3
- 208000029549 Muscle injury Diseases 0.000 abstract description 2
- 208000000112 Myalgia Diseases 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 277
- 239000000203 mixture Substances 0.000 description 251
- 230000001070 adhesive effect Effects 0.000 description 140
- 238000005266 casting Methods 0.000 description 84
- 230000000774 hypoallergenic effect Effects 0.000 description 82
- 239000004814 polyurethane Substances 0.000 description 82
- 229920002635 polyurethane Polymers 0.000 description 82
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- 241000124008 Mammalia Species 0.000 description 58
- 241000282412 Homo Species 0.000 description 57
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 55
- 238000011160 research Methods 0.000 description 55
- 239000000463 material Substances 0.000 description 35
- 238000000807 solvent casting Methods 0.000 description 28
- 239000002313 adhesive film Substances 0.000 description 27
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000002411 adverse Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 206010061623 Adverse drug reaction Diseases 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000001839 systemic circulation Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39634710P | 2010-05-27 | 2010-05-27 | |
| US61/396,347 | 2010-05-27 | ||
| PCT/US2011/038189 WO2011150239A2 (en) | 2010-05-27 | 2011-05-26 | Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2800716A1 CA2800716A1 (en) | 2011-12-01 |
| CA2800716C true CA2800716C (en) | 2019-11-05 |
Family
ID=44352274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2800716A Expired - Fee Related CA2800716C (en) | 2010-05-27 | 2011-05-26 | Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8563031B2 (enExample) |
| EP (1) | EP2575791B1 (enExample) |
| JP (2) | JP5948322B2 (enExample) |
| CN (1) | CN102970986B (enExample) |
| AU (1) | AU2011258146A1 (enExample) |
| CA (1) | CA2800716C (enExample) |
| WO (1) | WO2011150239A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3054931B1 (en) * | 2013-10-07 | 2020-12-23 | Teikoku Pharma USA, Inc. | Transdermal delivery device for managing pain comprising dexmedetomidine transdermal compositions |
| CN107028921A (zh) * | 2017-05-16 | 2017-08-11 | 蔡志浩 | 一种吡罗昔康巴布贴剂 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5989586A (en) | 1992-10-05 | 1999-11-23 | Cygnus, Inc. | Two-phase matrix for sustained release drug delivery device |
| JP2847578B2 (ja) | 1992-12-31 | 1999-01-20 | スンキョン インダストリイズ カンパニイ リミテッド | 皮膚浸透力を高めた医薬組成物 |
| AU6635294A (en) | 1993-04-22 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Transdermal antiinflammatory composition |
| DE4405898A1 (de) * | 1994-02-18 | 1995-08-24 | Schering Ag | Transdermale therapeutische Systeme enthaltend Sexualsteroide |
| JP3305101B2 (ja) * | 1994-03-29 | 2002-07-22 | 積水化学工業株式会社 | 経皮吸収製剤 |
| JPH08295624A (ja) * | 1995-04-26 | 1996-11-12 | Read Chem Kk | プラスター基剤、その製造方法、該基剤を使用した外用貼 付剤 |
| KR100294084B1 (ko) * | 1998-06-02 | 2001-09-22 | 성재갑 | 비-스테로이드성소염진통제의경피흡수투여용조성물및이를포함하는경피흡수투여용제형 |
| WO2001039753A1 (de) * | 1999-11-29 | 2001-06-07 | Lts Lohmann Therapie-Systeme Ag | Transdermale therapeutische systeme mit verbesserter stabilität und ein verfahren zu ihrer herstellung |
| US6645520B2 (en) * | 1999-12-16 | 2003-11-11 | Dermatrends, Inc. | Transdermal administration of nonsteroidal anti-inflammatory drugs using hydroxide-releasing agents as permeation enhancers |
| ES2559666T3 (es) | 2001-03-07 | 2016-02-15 | Hisamitsu Pharmaceutical Co., Inc. | Parche adhesivo |
| US20050020658A1 (en) * | 2002-11-21 | 2005-01-27 | Katsuyuki Inoo | Selective cyclooxygenase-2 inhibitor patch |
| US20040127531A1 (en) * | 2002-11-21 | 2004-07-01 | Lu Guang Wei | Adhesive coated sheet for dermal delivery of a selective cyclooxygenase-2 inhibitor |
| KR100552650B1 (ko) * | 2003-11-17 | 2006-02-20 | 아이큐어 주식회사 | 피록시캄 함유 소염진통용 플라스터 |
| AU2004290464A1 (en) * | 2003-11-19 | 2005-06-02 | Acrux Dds Pty Ltd | Method and composition for treatment or prophylaxis of amyloidosis disorders |
| US20070196457A1 (en) * | 2004-06-07 | 2007-08-23 | Jie Zhang | Two or more volatile solvent-containing compositions and methods for dermal delivery of drugs |
| DE102004062614B4 (de) * | 2004-12-24 | 2011-12-29 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System mit aktivierbarer Übersättigung und kontrollierter Permeationförderung sowie Verfahren zu dessen Herstellung |
| US20080226698A1 (en) * | 2007-03-16 | 2008-09-18 | Mylan Technologies, Inc. | Amorphous drug transdermal systems, manufacturing methods, and stabilization |
| EP2676680A1 (de) * | 2007-09-13 | 2013-12-25 | Basf Se | Verwendung von Hydrophobin-Polipeptiden als Penetrationsverstärker |
-
2011
- 2011-05-25 US US13/115,898 patent/US8563031B2/en not_active Expired - Fee Related
- 2011-05-26 EP EP11727855.6A patent/EP2575791B1/en not_active Not-in-force
- 2011-05-26 WO PCT/US2011/038189 patent/WO2011150239A2/en not_active Ceased
- 2011-05-26 CN CN201180031485.5A patent/CN102970986B/zh active Active
- 2011-05-26 CA CA2800716A patent/CA2800716C/en not_active Expired - Fee Related
- 2011-05-26 JP JP2013512249A patent/JP5948322B2/ja not_active Expired - Fee Related
- 2011-05-26 AU AU2011258146A patent/AU2011258146A1/en not_active Abandoned
-
2013
- 2013-10-21 US US14/059,375 patent/US20140046274A1/en not_active Abandoned
-
2015
- 2015-12-02 JP JP2015235438A patent/JP2016033163A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2011258146A1 (en) | 2012-12-20 |
| CA2800716A1 (en) | 2011-12-01 |
| US20110293721A1 (en) | 2011-12-01 |
| CN102970986B (zh) | 2015-06-03 |
| WO2011150239A2 (en) | 2011-12-01 |
| JP2016033163A (ja) | 2016-03-10 |
| EP2575791B1 (en) | 2018-08-08 |
| US20140046274A1 (en) | 2014-02-13 |
| JP5948322B2 (ja) | 2016-07-06 |
| WO2011150239A3 (en) | 2012-06-07 |
| US8563031B2 (en) | 2013-10-22 |
| JP2013527197A (ja) | 2013-06-27 |
| EP2575791A2 (en) | 2013-04-10 |
| CN102970986A (zh) | 2013-03-13 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20160505 |
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| MKLA | Lapsed |
Effective date: 20220526 |