WO1991006295A1 - Composition analgesique contenant du s(+) flurbiprofene optiquement pur - Google Patents

Composition analgesique contenant du s(+) flurbiprofene optiquement pur Download PDF

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Publication number
WO1991006295A1
WO1991006295A1 PCT/US1990/006442 US9006442W WO9106295A1 WO 1991006295 A1 WO1991006295 A1 WO 1991006295A1 US 9006442 W US9006442 W US 9006442W WO 9106295 A1 WO9106295 A1 WO 9106295A1
Authority
WO
WIPO (PCT)
Prior art keywords
flurbiprofen
pain
treatments
medicament
inflammation
Prior art date
Application number
PCT/US1990/006442
Other languages
English (en)
Inventor
William J. Wechter
James W. Young
Original Assignee
Sepracor, 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
Application filed by Sepracor, Inc. filed Critical Sepracor, Inc.
Publication of WO1991006295A1 publication Critical patent/WO1991006295A1/fr

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Classifications

    • 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
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
    • A61F13/53—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium
    • A61F13/539—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium characterised by the connection of the absorbent layers with each other or with the outer layers
    • 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
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
    • A61F13/53—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium
    • A61F2013/530802—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium characterized by the foam or sponge other than superabsorbent
    • 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
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
    • A61F13/53—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium
    • A61F13/539—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium characterised by the connection of the absorbent layers with each other or with the outer layers
    • A61F2013/5395—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium characterised by the connection of the absorbent layers with each other or with the outer layers with thermoplastic agent, i.e. softened by heat

Definitions

  • Flurbiprofen is a drug belonging to the general class of compounds known as non-steroidal antiinflammatory drugs (NSAIDs). NSAIDs as a class exhibit analgesic, anti-inflammatory and antipyretic activity, and include well-known commercial
  • pain-relievers such as ibuprofen and aspirin.
  • Flurbiprofen is a very potent NSAID. It is believed that flurbiprofen inhibits biosynthesis of prostaglandins.
  • Flurbiprofen is a racemic mixture. That is, it is a mixture of optical isomers, called enantiomers. Enantiomers are structurally identical compounds which differ only in that one Isomer is a mirror image of the other and the mirror images cannot be superimposed. This phenomenon is known as
  • the present invention relates to a method of treating pain and inflammation in an individual comprising administering to the individual an analgesic, anti-inflammatory amount of the S(+)
  • the method is useful in treating pain associated with toothaches, sprains, joint pain and surgical pain, for example, dental pain, (e.g., after periodontal surgery), and
  • an analgesic and anti-inflammatory composition which is non-irritating and a potent pain killer.
  • flurbiprofen is particularly useful for this
  • the present method provides a safe, highly effective method for treating severe pain and inflammation, such as pain and inflammation associated with peridontal and/or opthalmic surgery or other treatment. Detail ed Description of the Invention
  • the present invention relies on the analgesic activity of the dextrorotatory enantiomer of flurbiprofen, referred to as S(+) flurbiprofen, to provide enhanced relief from pain, such as pain associated with toothaches, sprains, joint pain and surgical pain, particularly pain associated with dental surgery (e.g., periodontal surgery) and with ophthalmic surgery (e.g., cataract surgery).
  • S(+) flurbiprofen which is substantially free of its R(-) enantiomer is administered alone, or in combination with other drugs in adjunctive treatment to an individual in whom pain relief is desired.
  • m S(+) flurbiprofen refers to the dextrorotatory or S(+) isomer of
  • S(+) flurbiprofen is administered to an individual suffering from pain and/or inflammation.
  • S(+) flurbiprofen is administered to an individual after periodontal surgery, or after cataract surgery, to reduce, ameliorate or eliminate pain and inflammation resulting from the surgery.
  • S(+) flurbiprofen is administered prophylac tically, that is, before the surgery to reduce pain after the operation.
  • the drug can be administered orally, by subcutaneous or other injection, intravenously, topically, parenterally, transdermally, rectally or via an implanted reservoir containing S(+) flurbiprofen.
  • the quantity of the drug to be administered will be determined on an individual basis, and will be based at least in part on consideration of the individual's size, the severity of the symptoms to be treated and the result sought. In general, quantities of S(+) flurbiprofen sufficient to reduce, ameliorate or eliminate the pain will be administered.
  • a dose in the range of about 2-3 mg per kg of body weight per day will be
  • S(+) flurbiprofen can be administered along with one or more other drugs.
  • codein, hydrocodone or caffeine can be given with or in close temporal proximity to administration of S(+) flurbiprofen.
  • the two (or more) drugs can be administered In one composition or as two separate entities. For example, they can be administered in a single capsule, tablet, powder, liquid, etc. or as individual compounds.
  • the components included in a particular composition, in addition to S(+) flurbiprofen and another drug or drugs, are determined primarily by the manner in which the composition is to be administered.
  • a composition to be administered orally in tablet form can include, in addition to the drugs, a filler (e.g., lactose), a binder (e.g., carboxymethyl cellulose, gum arable, gelatin), an adjuvant, a flavoring agent, a coloring agent and a coating material (e.g., wax or a plasticizer).
  • a composition to be administered in liquid form can include the combination of drugs and, optionally, an emulsifying agent, a flavoring agent and/or a coloring agent.
  • the composition can also contain a small amount of its R(-) enantiomer.
  • the optically pure isomer has a higher melting point than a racemic mixture which contains a small amount of the non-active R(-) isomer.
  • a mixture having a lower melting point is more readily absorbed by the body, because of its higher dissolution rate resulting in higher bloodstream levels than the pure isomer.
  • a mixture containing 90% of the S(+) isomer can 10% of the R(-) isomer (i.e., has an enantiomeric excess of 80%) is particularly useful because it has the lowest melting point.
  • S(+) flurbiprofen alone or in combination with another drug(s) is administered to an individual periodically as necessary to reduce or ameliorate symptoms of the pain being treated.
  • the length of time during which the drugs are administered and the dosage will depend on the pain being treated, the type and severity of the symptoms, and the physical condition of the Individual being treated.
  • Example 2 details a protocol for producing the S(+) enantiomer of flurbiprofen. This Example is not intended to be limiting of the invention.
  • N , N- Dimethylethanolamine ester (0.355 moles) was di s s o lved in 500 mis of diethyl ether and stirred in a flask cooled to 0oC by an ice/water bath. To this solution was added dropwise a solution of 1.0 equivalents (0.355 moles, 33.6 mis) of dimethyl sulphate, dissolved in 100 mis diethyl ether over approximately 60 minutes. The ice bath was then removed, and the reaction mixture allowed to stir at 20oC-22oC for 18 hours.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Du S(+) flurbiprofène optiquement pur essentiellement dépourvu du R(-) énantiomère forme un analgésique puissant pour soulager la douleur et des inflammations chez des êtres humains et des animaux. Un procédé et une composition utilisent le S(+) énantiomère de flurbiprofène optiquement pur pour traiter des algies et des inflammations.
PCT/US1990/006442 1989-11-06 1990-11-06 Composition analgesique contenant du s(+) flurbiprofene optiquement pur WO1991006295A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43280889A 1989-11-06 1989-11-06
US432,808 1989-11-06

Publications (1)

Publication Number Publication Date
WO1991006295A1 true WO1991006295A1 (fr) 1991-05-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/006442 WO1991006295A1 (fr) 1989-11-06 1990-11-06 Composition analgesique contenant du s(+) flurbiprofene optiquement pur

Country Status (2)

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AU (1) AU6758990A (fr)
WO (1) WO1991006295A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0527830A1 (fr) * 1990-05-18 1993-02-24 Analgesic Associates Reponse antipyretique entretenue/amelioree
WO1993010771A1 (fr) * 1991-12-05 1993-06-10 Alfatec-Pharma Gmbh Medicament a effet retard contenant du flurbiprofene et son utilisation
WO1993010766A1 (fr) * 1991-12-05 1993-06-10 Alfatec-Pharma Gmbh Medicament a effet immediat contenant du flurbiprofene et son utilisation
WO1994014449A1 (fr) * 1992-12-21 1994-07-07 The Procter & Gamble Company Compositions contenant de la cafeine et s(+)-ibuprofene ou s(+)-flurbiprofene ou s(+)-cetoprofene
WO1995007079A1 (fr) * 1993-09-07 1995-03-16 The Procter & Gamble Company Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine
WO1997023205A1 (fr) * 1995-12-22 1997-07-03 Minnesota Mining And Manufacturing Company Dispositif transdermique destine a l'administration du flurbiprofene
EP1013275A2 (fr) * 1991-11-26 2000-06-28 Sepracor, Inc. Procédés et compositions destinés à traiter l'hypertension, l'angine de poitrine et d'autres troubles à l'aide de (-) amlodipine optiquement pure
EP1022025A2 (fr) * 1991-06-26 2000-07-26 Sepracor, Inc. Methodes et compositions pour le traitement des vomissements, de la nausee et d'autres troubles faisant appel a l'ondansetron optiquement pur R(+)
US6280891B2 (en) 1994-05-04 2001-08-28 Hologram Industries S.A. Multi-layer assembly and method for marking articles and resulting marked articles
EP0607128B2 (fr) † 1990-09-12 2007-02-21 Paz Arzneimittel- Entwicklungsgesellschaft Mbh Medicament, sa production et sont utilisation comme analgesique et/ou anti-inflammatoire pour animaux et etres humains
JP2014043450A (ja) * 2013-10-08 2014-03-13 Techfields Biochem Co Ltd 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
WO2015145163A1 (fr) * 2014-03-26 2015-10-01 Aesica Pharmaceuticals Limited Procédé de fabrication de s-(+)-flurbiprofène
CN111840215A (zh) * 2019-04-30 2020-10-30 北京蓝丹医药科技有限公司 一种氟比洛芬注射液与容器的组合
WO2023279995A1 (fr) * 2021-07-06 2023-01-12 石家庄迪斯凯威医药科技有限公司 Classe de composés de sel d'ammonium quaternaire anti-cancer de la vessie et leur utilisation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3814887C1 (fr) * 1988-05-02 1989-09-21 Medice Chem.-Pharm. Fabrik Puetter Gmbh & Co Kg, 5860 Iserlohn, De

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3814887C1 (fr) * 1988-05-02 1989-09-21 Medice Chem.-Pharm. Fabrik Puetter Gmbh & Co Kg, 5860 Iserlohn, De

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF PHARMACEUTICAL SCIENCES, Vol. 77, No. 8, August 1988, (Washington DC, US), F. JAMALI et al., "Streoselective Pharmacokinetics of Flurbiprofen in Humans and Rats", pages 666-669. *
JOURNAL OF PHARMACEUTICAL SCIENCES, Vol. 78, No. 8, August 1989, (Washington DC, US), B.W. BERRY et al., "Enantiomeric Interaction of Flurbiprofen in the Rat", pages 632-634. *
MED. LETT. DRUGS THER., Vol. 29, No. 742, 1987, "Flurbiprofen - An Ophthalmic NSAID", pages 58-59. *
NIPPON GANKA GAKKAI ZASSHI, Vol. 91, No. 5, 1987, (Tokyo, JP), H. TSUCHISAKA et al., "Effects of Topical Flurbiprofen in Planned-Extracapsular Castaract Extraction by Double Blind Method", pages 570-578. *
SCAND. J. RHEUMATOLOGY, Suppl. 14, 1976, (Stockholm, SE), H. WILLIAMS et al., "Ophthalmic Screening of Patients Receiving Ketoprofen of Flurbiprofen Medication for Inflammatory and Degenerative Joint Diseases", pages 85-92. *
SHIKAI TENBO, Vol. 53, No. 5, 1979, (Tokyo, JP), I. ISHAKAWA et al., Clinical Use of a Flurbiprofen Preparation (Froben) for Various Pains in Operative Dentistry", pages 875-881, (Tittle Translated by Medline). *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0527830A1 (fr) * 1990-05-18 1993-02-24 Analgesic Associates Reponse antipyretique entretenue/amelioree
EP0527830A4 (en) * 1990-05-18 1993-03-24 Analgesic Associates Sustained/enhanced antipyretic response
EP0607128B2 (fr) † 1990-09-12 2007-02-21 Paz Arzneimittel- Entwicklungsgesellschaft Mbh Medicament, sa production et sont utilisation comme analgesique et/ou anti-inflammatoire pour animaux et etres humains
EP1022025A3 (fr) * 1991-06-26 2002-06-05 Sepracor, Inc. Methodes et compositions pour le traitement des vomissements, de la nausee et d'autres troubles faisant appel a l'ondansetron optiquement pur R(+)
EP1022025A2 (fr) * 1991-06-26 2000-07-26 Sepracor, Inc. Methodes et compositions pour le traitement des vomissements, de la nausee et d'autres troubles faisant appel a l'ondansetron optiquement pur R(+)
EP1013275A2 (fr) * 1991-11-26 2000-06-28 Sepracor, Inc. Procédés et compositions destinés à traiter l'hypertension, l'angine de poitrine et d'autres troubles à l'aide de (-) amlodipine optiquement pure
EP1013275A3 (fr) * 1991-11-26 2001-01-10 Sepracor, Inc. Procédés et compositions destinés à traiter l'hypertension, l'angine de poitrine et d'autres troubles à l'aide de (-) amlodipine optiquement pure
WO1993010771A1 (fr) * 1991-12-05 1993-06-10 Alfatec-Pharma Gmbh Medicament a effet retard contenant du flurbiprofene et son utilisation
WO1993010766A1 (fr) * 1991-12-05 1993-06-10 Alfatec-Pharma Gmbh Medicament a effet immediat contenant du flurbiprofene et son utilisation
WO1994014449A1 (fr) * 1992-12-21 1994-07-07 The Procter & Gamble Company Compositions contenant de la cafeine et s(+)-ibuprofene ou s(+)-flurbiprofene ou s(+)-cetoprofene
AU672279B2 (en) * 1992-12-21 1996-09-26 Procter & Gamble Company, The Compositions containing caffeine and S(+)-ibuprofen or S(+)-flurbiprofen or S(+)-ketoprofen
WO1995007079A1 (fr) * 1993-09-07 1995-03-16 The Procter & Gamble Company Compositions contenant un sel d'acide amine d'agents anti-inflammatoires non steroidiens a base d'acide propionique et de la cafeine
US6280891B2 (en) 1994-05-04 2001-08-28 Hologram Industries S.A. Multi-layer assembly and method for marking articles and resulting marked articles
US6086911A (en) * 1995-12-22 2000-07-11 3M Innovative Properties Company Drug delivery device
US5702720A (en) * 1995-12-22 1997-12-30 Minnesota Mining And Manufacturing Company Transdermal device for the delivery of flurbiprofen
WO1997023206A1 (fr) * 1995-12-22 1997-07-03 Minnesota Mining And Manufacturing Company Dispositif d'administration de medicament
WO1997023205A1 (fr) * 1995-12-22 1997-07-03 Minnesota Mining And Manufacturing Company Dispositif transdermique destine a l'administration du flurbiprofene
JP2014043450A (ja) * 2013-10-08 2014-03-13 Techfields Biochem Co Ltd 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
WO2015145163A1 (fr) * 2014-03-26 2015-10-01 Aesica Pharmaceuticals Limited Procédé de fabrication de s-(+)-flurbiprofène
CN111840215A (zh) * 2019-04-30 2020-10-30 北京蓝丹医药科技有限公司 一种氟比洛芬注射液与容器的组合
WO2023279995A1 (fr) * 2021-07-06 2023-01-12 石家庄迪斯凯威医药科技有限公司 Classe de composés de sel d'ammonium quaternaire anti-cancer de la vessie et leur utilisation

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